Jin-song Yang *

Name:

Organization: Sichuan University

Department: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital

Title:

TOPICS

Organic Chemistry

Oligosaccharide Synthesis

Chemicals
References

Stereoselective synthesis of aryl 1,2-cis-furanosides and its application to the synthesis of the carbohydrate portion of antibiotic hygromycin A

Co-reporter:Yuan Xu, Hua-Chao Bin, Fu Su, Jin-Song Yang

Tetrahedron Letters 2017 Volume 58, Issue 16(Issue 16) pp:

Publication Date(Web):19 April 2017

DOI:10.1016/j.tetlet.2017.02.079

•A approach to the construction of aryl 1,2-cis-furanosidic bonds is developed.•Aryl 1,2-cis-furanosides are synthesized using Quin-substituted thiofuranosides.•The method is demonstrated by preparation of the sugar portion of hygromycin A.An efficient methodology for the synthesis of aryl 1,2-cis-furanosidic linkages has been developed with 2-quinolinecarbonyl (Quin) group substituted furanose ethyl thioglycosides as glycosyl donors. The method permits a wide range of phenol acceptors to be used, thus resulting in the formation of structurally diverse phenol furanosides in good to excellent chemical yields with complete 1,2-cis anomeric selectivity. The synthetic utility of the approach has been demonstrated by concise preparation of the carbohydrate portion of antibiotic hygromycin A.Download high-res image (132KB)Download full-size image

Total Synthesis of Marine Glycosphingolipid Vesparioside B

Co-reporter:Peng-Cheng Gao; San-Yong Zhu; Hui Cao;Jin-Song Yang

Journal of the American Chemical Society 2016 Volume 138(Issue 5) pp:1684-1688

Publication Date(Web):January 19, 2016

DOI:10.1021/jacs.5b12589

The first total synthesis of a major component of marine glycolipid vesparioside B (Scheme 1, 1, R1 = n-C22H45, R2 = n-C14H29) has been accomplished through a convergent [4 + 3] coupling strategy. Key steps included stereoselective installment of a set of challenging 1,2-cis-glycoside bonds. A 2-quinolinecarbonyl-assisted α-galactosylation and a novel β-arabinosylation were developed, respectively, to synthesize the α-galactofuranosidic and the β-arabinopyranosidic linkages. Furthermore, a 4,6-O-benzylidene-controlled α-galactopyranosylation reaction allowed the efficient connection of the left tetrasaccharide donor 2 with the right disaccharide lipid acceptor 3, hence leading to the total synthesis of 1.

Synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-d-proline relevant to the cell wall O-glycans of green alga Chlamydomonas reinhardtii

Co-reporter:Kai Zhu, Jin-Song Yang

Tetrahedron 2016 Volume 72(Issue 22) pp:3113-3123

Publication Date(Web):2 June 2016

DOI:10.1016/j.tet.2016.04.038

The synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-d-proline 1 and 2 with unusual glycan motifs has been achieved efficiently. The assembly of the synthetically challenging 1,2-cis linked arabino- and galactofuranoside frameworks within the targets was realized by the use of a 2-quinolinecarbonyl-assisted 1,2-cis furanosylation approach.

Stereoselective Synthesis of -3-Deoxy-D-manno-oct-2-ulosonic Acid (-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors

Co-reporter:Jia-Sheng Huang;Wei Huang;Xue Meng;Xin Wang;Peng-Cheng Gao;Dr. Jin-Song Yang

Angewandte Chemie International Edition 2015 Volume 54( Issue 37) pp:

Publication Date(Web):

DOI:10.1002/anie.201505176

Abstract

An efficient methodology for the synthesis of α-Kdo glycosidic bonds has been developed with 5,7-O-di-tert-butylsilylene (DTBS) protected Kdo ethyl thioglycosides as glycosyl donors. The approach permits a wide scope of acceptors to be used, thus affording biologically significant Kdo glycosides in good to excellent chemical yields with complete α-selectivity. The synthetic utility of an orthogonally protected Kdo donor has been demonstrated by concise preparation of two α-Kdo-containing oligosaccharides.

Stereoselective Synthesis of -3-Deoxy-D-manno-oct-2-ulosonic Acid (-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors

Co-reporter:Jia-Sheng Huang;Wei Huang;Xue Meng;Xin Wang;Peng-Cheng Gao;Dr. Jin-Song Yang

Angewandte Chemie 2015 Volume 127( Issue 37) pp:

Publication Date(Web):

DOI:10.1002/ange.201505176

Abstract

Influence of Silyl Protections on the Anomeric Reactivity of Galactofuranosyl Thioglycosides and Application of the Silylated Thiogalactofuranosides to One-Pot Synthesis of Diverse β-d-Oligogalactofuranosides

Co-reporter:Shuai Wang, Xue Meng, Wei Huang, and Jin-Song Yang

The Journal of Organic Chemistry 2014 Volume 79(Issue 21) pp:10203-10217

Publication Date(Web):October 13, 2014

DOI:10.1021/jo5018684

We describe in this paper the tuning effect of silyl protecting groups on the donor reactivity of galactofuranosyl phenyl thioglycosides. Silyl ethers on the galactofuranose ring are found to have an arming effect on the glycosylation reactivity, but the cyclic 3,5-acetal protecting group decreases the reactivity. The reactive phenyl 2,6-di-O-Bz-3,5-di-O-TBS-1-thio-β-d-galactofuranoside 3 is proved to be a useful glycosyl building block. By taking advantage of this donor, we achieved the highly efficient one-pot solution-phase assembly of a panel of β-d-galactofuranosyl tri- and tetrasaccharides possessing diverse glycosidic linkages.

First Total Synthesis of the Proposed Structure of Batatin VI

Co-reporter:San-Yong Zhu, Jia-Sheng Huang, Shan-Shan Zheng, Kai Zhu, and Jin-Song Yang

Organic Letters 2013 Volume 15(Issue 16) pp:4154-4157

Publication Date(Web):July 30, 2013

DOI:10.1021/ol4020255

The first total synthesis of batatin VI, an architecturally novel resin glycoside dimer, has been achieved via a convergent [5 + 3] glycosidic coupling approach. An improved protocol for the construction of the key 18-membered macrolactone core using a Keck macrolactonization method was introduced. However, the synthesized compound was not identical to the natural batatin VI.

β-Arabinofuranosylation Using 5-O-(2-Quinolinecarbonyl) Substituted Ethyl Thioglycoside Donors

Co-reporter:Qiang-Wei Liu, Hua-Chao Bin, and Jin-Song Yang

Organic Letters 2013 Volume 15(Issue 15) pp:3974-3977

Publication Date(Web):July 23, 2013

DOI:10.1021/ol401755e

A new β-stereoselective d- and l-arabinofuranosylation method has been developed employing 5-O-(2-quinolinecarbonyl) substituted arabinosyl ethyl thioglycosides as glycosyl donors. The approach allows a wide range of acceptor substrates to be used; the β-selectivity is good-to-excellent. Stereoselective synthesis of a mannose-capped octasaccharide portion from a mycobacterial cell wall polysaccharide was then carried out to demonstrate the utility of this methodology.

Tuning Effect of Silyl Protecting Groups on the Glycosylation Reactivity of Arabinofuranosyl Thioglycosides

Co-reporter:Xing-Yong Liang, Hua-Chao Bin, and Jin-Song Yang

Organic Letters 2013 Volume 15(Issue 11) pp:2834-2837

Publication Date(Web):May 17, 2013

DOI:10.1021/ol401166x

The tuning effect of silyl protecting groups on the glycosylation reactivity of arabinofuranosyl phenyl thioglycoside donors is presented. Silyl ethers on the 3-, 5-, and 3,5-positions of the arabinofuranose ring are found to have an arming effect on the donor reactivity, whereas the cyclic 3,5-acetal type protecting groups reduce the reactivity.

Regioselective Glycosylation Method Using Partially Protected Arabino- and Galactofuranosyl Thioglycosides as Key Glycosylating Substrates and Its Application to One-Pot Synthesis of Oligofuranoses

Co-reporter:Li-Min Deng, Xia Liu, Xing-Yong Liang, and Jin-Song Yang

The Journal of Organic Chemistry 2012 Volume 77(Issue 7) pp:3025-3037

Publication Date(Web):February 27, 2012

DOI:10.1021/jo300084g

We describe in this paper the development of a novel regioselective furanosylation methodology using partially protected furanosyl thioglycosides as central glycosylating building blocks and its application in the efficient one-pot synthesis of a series of linear and branched-type arabino- and galactofuranoside fragments structurally related to the cell wall polysaccharides of Mycobacterium tuberculosis, Streptococcus pneumoniae serostype 35A, and sugar beet.

A Diastereoselective Cyclic Imine Cycloaddition Strategy To Access Polyhydroxylated Indolizidine Skeleton: Concise Syntheses of (+)-/(−)-Lentiginosines and (−)-2-epi-Steviamine

Co-reporter:Jia Shao and Jin-Song Yang

The Journal of Organic Chemistry 2012 Volume 77(Issue 18) pp:7891-7900

Publication Date(Web):September 4, 2012

DOI:10.1021/jo3010777

We describe in this paper the development of a novel diastereoselective cyclic imine cycloaddition strategy to access the polyhydroxylated indolizidine skeleton and its application in the concise syntheses of (+)-/(−)-lentiginosines and (−)-2-epi-steviamine.

Synthesis of tetra- and hexasaccharide fragments corresponding to the O-antigenic polysaccharide of Klebsiella pneumoniae

Co-reporter:San-Yong Zhu, Jin-Song Yang

Tetrahedron 2012 68(20) pp: 3795-3802

Publication Date(Web):

DOI:10.1016/j.tet.2012.03.074

Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis

Co-reporter:Xing-Yong Liang, Li-Min Deng, Xia Liu, Jin-Song Yang

Tetrahedron 2010 66(1) pp: 87-93

Publication Date(Web):

DOI:10.1016/j.tet.2009.11.038

Total Synthesis of Batatoside L

Co-reporter:Lin Xie, San-Yong Zhu, Xiao-Qiu Shen, Li-Li He and Jin-Song Yang

The Journal of Organic Chemistry 2010 Volume 75(Issue 16) pp:5764-5767

Publication Date(Web):July 28, 2010

DOI:10.1021/jo101231r

The total synthesis of batatoside L (1), a resin glycoside possessing cytotoxicity against laryngeal carcinoma cells, has been completed in a highly convergent manner. The most crucial step in this total synthesis was the efficient construction of the 18-membered macrolactone framework through the Corey−Nicolaou macrolactonization approach.

Synthetic studies on the trisaccharide intermediate of resin glycoside merremoside H2

Co-reporter:Xiao-Qiu Shen, Lin Xie, Liang Gao, Li-Li He, Qian Yang, Jin-Song Yang

Carbohydrate Research 2009 Volume 344(Issue 15) pp:2063-2068

Publication Date(Web):12 October 2009

DOI:10.1016/j.carres.2009.08.005

A protected trisaccharide imidate, 2,3-di-O-acetyl-4,6-O-benzylidene-β-d-glucopyranosyl-(1→3)-2-O-chloroacetyl-3-O-benzyl-4-isobutyryl-α-l-rhamnopyranosyl-(1→4)-2-O-isobutyryl-α-l-rhamnopyranosyl trichloroacetimidate (1), has been synthesized by a block synthesis approach. Compound 1 can serve as a key intermediate in the total synthesis of resin glycoside merremoside H2.

Microwave-assisted palladium-catalyzed cross-coupling reactions between pyranoid glycals and aryl bromides. Synthesis of 2′-deoxy C-aryl-β-glycopyranosides

Co-reporter:Ming Lei, Liang Gao, Jin-Song Yang

Tetrahedron Letters 2009 50(36) pp: 5135-5138

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.06.116

Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-α-l-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D

Co-reporter:Qian Yang, Ming Lei, Qin-Jian Yin, Jin-Song Yang

Carbohydrate Research 2007 Volume 342(Issue 9) pp:1175-1181

Publication Date(Web):2 July 2007

DOI:10.1016/j.carres.2007.03.001

The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-α-l-rhamnopyranosides was selectively acylated in 56–78% yields by reaction with 1.1 equiv of acyl chloride in the presence of 1.5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D.