Further studies in alpha-C-mannosylation promoted by samarium diiodide

被引：20

作者：

Jarreton, O ^{[1
]}

Skrydstrup, T ^{[1
]}

Beau, JM ^{[1
]}

机构：

[1] CNRS,INST CHIM MOL ORSAY,LAB SYNTH BIOMOL,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(97)00206-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mannosyl pyridylsulfones with varying C2-OH protecting groups were reacted with cyclohexanone in the presence of SmI2. With SiMe(2)tBu and Bn, high yields of an alpha-C-mannoside were obtained. In the former case no beta-elimination was observed. The relative configuration of the major diastereomer obtained upon coupling with aldehydes was determined. (C) 1997 Elsevier Science Ltd.

引用

页码：1767 / 1770

页数：4

共 12 条

[1] Synthesis of glycosyl chlorides with acid-labile protecting groups [J].

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (28) :4903-4906

[2]

JARRETON O, 1996, J CHEM SOC CHEM COMM, P1661

[3] SIMPLE GENERATION OF A REACTIVE GLYCOSYL-LITHIUM DERIVATIVE [J].

LANCELIN, JM ;

MORINALLORY, L ;

SINAY, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (06) :355-356

[4]

Lesimple P, 1994, Bioorg Med Chem, V2, P1319, DOI 10.1016/S0968-0896(00)82082-9

[5] A HIGHLY STEREOSELECTIVE SYNTHESIS OF 1,2-TRANS-C-GLYCOSIDES VIA GLYCOSYL SAMARIUM(III) COMPOUNDS [J].

MAZEAS, D ;

SKRYDSTRUP, T ;

BEAU, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08) :909-912

[6] SAMARIUM IODIDE INDUCED INTRAMOLECULAR C-GLYCOSIDE FORMATION - EFFICIENT RADICAL FORMATION IN THE ABSENCE OF AN ADDITIVE [J].

MAZEAS, D ;

SKRYDSTRUP, T ;

DOUMEIX, O ;

BEAU, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (13) :1383-1386

[7] A NOVEL 1,3 0-]C SILYL REARRANGEMENT IN CARBOHYDRATE-CHEMISTRY - SYNTHESIS OF ALPHA-D-GLYCOPYRANOSYLTRIMETHYLSILANES [J].

PEDRETTI, V ;

VEYRIERES, A ;

SINAY, P .

TETRAHEDRON, 1990, 46 (01) :77-88

[8] Filipin III: Configuration assignment and confirmation by synthetic correlation [J].

Richardson, TI ;

Rychnovsky, SD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4219-4231

[9] ANALYSIS OF 2 C-13 NMR CORRELATIONS FOR DETERMINING THE STEREOCHEMISTRY OF 1,3-DIOL ACETONIDES [J].

RYCHNOVSKY, SD ;

ROGERS, B ;

YANG, G .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) :3511-3515

[10]

SKRYDSTRUP T, UNPUB

← 1 2 →