Glycosylation Reaction of Thioglycosides by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter

被引：11

作者：

Kajimoto, Tetsuya ^{[1
]}

Morimoto, Koji ^{[1
]}

Ogawa, Ryosuke ^{[2
]}

Dohi, Toshifumi ^{[2
]}

Kita, Yasuyuki ^{[1
,2
]}

机构：

[1] Ritsumeikan Univ, Res Org Sci & Technol, 1-1-1 Nojihigashi, Kusatsu, Shiga 5258577, Japan

[2] Ritsumeikan Univ, Coll Pharmaceut Sci, 1-1-1 Nojihigashi, Kusatsu, Shiga 5258577, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2016年 / 64卷 / 07期

基金：

日本学术振兴会;

关键词：

glycosylation; hypervalent iodine reagent; thioglycoside; ODORLESS BENZENETHIOLS; MEDIATED ACTIVATION; POLYVALENT IODINE; ORGANIC-SYNTHESIS; GLYCOSIDES; DONORS; CHEMISTRY; OLIGOSACCHARIDE; PRODUCT; LINKAGE;

D O I：

10.1248/cpb.c16-00203

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Thioglycosides are available donors in glycosylation due to the stability of the anomeric C-S bond under general reaction conditions of protection and deprotection, and offer orthogonality in their activation. We report now that the hypervalent iodine effectively induced glycosylation reaction of thioglycosides with various alcohols. This method features a high efficiency, completion in a short time, and proceeding under very mild conditions.

引用

页码：838 / 844

页数：7

共 43 条

[31] CARBOHYDRATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF 16-MEMBERED-RING MACROLIDE ANTIBIOTICS .5. TOTAL SYNTHESIS OF O-MYCINOSYLTYLONOLIDE - SYNTHESIS OF KEY INTERMEDIATES
NICOLAOU, KC
PAVIA, MR
SEITZ, SP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) : 2027 - 2029
[32] AN EFFICIENT APPROACH TO O-GLYCOSIDES THROUGH CUBR2 -BU4NBR MEDIATED ACTIVATION OF GLYCOSIDES
SATO, S
MORI, M
ITO, Y
OGAWA, T
[J]. CARBOHYDRATE RESEARCH, 1986, 155 : C6 - C10
[33] Organic polyvalent iodine compounds
Stang, PJ
Zhdankin, VV
[J]. CHEMICAL REVIEWS, 1996, 96 (03) : 1123 - 1178
[34] Hypervalent iodine reagents for the oxidation of alcohols and their application to complex molecule synthesis
Tohma, H
Kita, Y
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) : 111 - 124
[35] Tohma H, 2003, TOP CURR CHEM, V224, P209
[36] A STEREOSELECTIVE SYNTHESIS OF DIGITOXIN - ON CARDIOACTIVE STEROIDS .13.
TSAI, TYR
JIN, H
WIESNER, K
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07): : 1403 - 1405
[37] REINVESTIGATION OF THE PREPARATION OF CHOLESTERYL 2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSIDE
VANCLEVE, JW
[J]. CARBOHYDRATE RESEARCH, 1979, 70 (01) : 161 - 164
[38] Varvoglis A., 1997, HYPERVALENT IODINE O
[39] IODONIUM ION PROMOTED REACTIONS AT THE ANOMERIC CENTER .2. AN EFFICIENT THIOGLYCOSIDE MEDIATED APPROACH TOWARD THE FORMATION OF 1,2-TRANS LINKED GLYCOSIDES AND GLYCOSIDIC ESTERS
VEENEMAN, GH
VANLEEUWEN, SH
VANBOOM, JH
[J]. TETRAHEDRON LETTERS, 1990, 31 (09) : 1331 - 1334
[40] Visible Light Mediated Activation and O-Glycosylation of Thioglycosides
Wever, Walter J.
Cinelli, Maris A.
Bowers, Albert A.
[J]. ORGANIC LETTERS, 2013, 15 (01) : 30 - 33

← 1 2 3 4 5 →