S-Adamantyl Group Directed Site-Selective Acylation: Applications in Streamlined Assembly of Oligosaccharides

被引：32

作者：

Blaszczyk, Stephanie A. ^{[1
,2
]}

Xiao, Guozhi ^{[1
]}

Wen, Peng ^{[1
]}

Hao, Hua ^{[3
]}

Wu, Jessica ^{[1
]}

Wang, Bo ^{[1
]}

Carattino, Francisco ^{[3
]}

Li, Ziyuan ^{[1
]}

Glazier, Daniel A. ^{[2
]}

McCarty, Bethany J. ^{[2
]}

Liu, Peng ^{[3
]}

Tang, Weiping ^{[1
,2
]}

机构：

[1] Univ Wisconsin, Sch Pharm, 777 Highland Ave, Madison, WI 53705 USA

[2] Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA

[3] Univ Pittsburgh, Dept Chem, 219 Parkman Ave, Pittsburgh, PA 15260 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 28期

关键词：

acylation; carbohydrates; glycosylation; noncovalent interactions; synthetic methods; REGIOSELECTIVE ALKYLATION; BORONIC ESTERS; CARBOHYDRATE; CATALYST; FUNCTIONALIZATION; THIOGLYCOSIDES; GLYCOSYLATION; RECOGNITION; SILYLATION; ACTIVATION;

D O I：

10.1002/anie.201903587

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The site-selective functionalization of carbohydrates is an active area of research. Reported here is the surprising observation that the sterically encumbered adamantyl group directed site-selective acylation at the C2 position of S-glycosides through dispersion interactions between the adamantyl C-H bonds and the pi system of the cationic acylated catalyst, which may have broad implications in many other chemical reactions. Because of their stability, chemical orthogonality, and ease of activation for glycosylation, the site-selective acylation of S-glycosides streamlines oligosaccharide synthesis and will have wide applications in complex carbohydrate synthesis.

引用

页码：9542 / 9546

页数：5

共 35 条

[1] Chiral Copper(II) Complex-Catalyzed Reactions of Partially Protected Carbohydrates [J].

Allen, C. Liana ;

Miller, Scott J. .

ORGANIC LETTERS, 2013, 15 (24) :6178-6181

[2] The biology of NKT cells [J].

Bendelac, Albert ;

Savage, Paul B. ;

Teyton, Luc .

ANNUAL REVIEW OF IMMUNOLOGY, 2007, 25 :297-336

[3] Chemical glycobiology [J].

Bertozzi, CR ;

Kiessling, LL .

SCIENCE, 2001, 291 (5512) :2357-2364

[4] Benzotetramisole: A remarkably enantioselective acyl transfer catalyst [J].

Birman, VB ;

Li, XM .

ORGANIC LETTERS, 2006, 8 (07) :1351-1354

[5] α-selective sialylations at-78 °C in nitrile solvents with a 1-adamantanyl thiosialoside [J].

Crich, David ;

Li, Wenju .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) :7794-7797

[6] REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES [J].

DAVID, S ;

HANESSIAN, S .

TETRAHEDRON, 1985, 41 (04) :643-663

[7] Odorless Access to Thioglycosides for Oligosaccharide Synthesis: Their Design and Advanced Procedures for Thioglycosidation [J].

Dohi, Hirofumi ;

Nishida, Yoshihiro .

TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 2014, 26 (151) :119-130

[8] Regioselective, Tin-Free Sulfation of Unprotected Hexopyranosides by Using Phenylboronic Acid [J].

Fukuhara, Kenji ;

Shimada, Naoyuki ;

Nishino, Takashi ;

Kaji, Eisuke ;

Makino, Kazuishi .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (05) :902-905

[9] Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics [J].

Gijsen, HJM ;

Qiao, L ;

Fitz, W ;

Wong, CH .

CHEMICAL REVIEWS, 1996, 96 (01) :443-473

[10] Site-Selective Reactions with Peptide-Based Catalysts [J].

Giuliano, Michael W. ;

Miller, Scott J. .

SITE-SELECTIVE CATALYSIS, 2016, 372 :157-201

← 1 2 3 4 →