Fragmentation of carbohydrate anomeric alkoxyl radicals.: Synthesis of highly functionalized chiral vinyl sulfones

被引：17

作者：

Alonso-Cruz, CR

León, EI

Ortiz-López, FJ

Rodríguez, MS

Suárez, E

机构：

[1] CSIC, Inst Prod Nat & Agrobiol, San Cristobal la Laguna 32806, Tenerife, Spain

[2] Univ La Laguna, Dept Quim Organ, Tenerife, Spain

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 32期

关键词：

radical reaction; alkoxyl radical; carbohydrate; vinyl sulfone;

D O I：

10.1016/j.tetlet.2005.06.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of derivatives of 3-acetyl-D-glucal, 3-acetyl-L-rhamnal, 3-acetyl-D-galactal, and 3-acetyl-D-lactal with sodium benzenesulfinate in acid medium catalyzed by HgSO4 afforded diastereoisomeric mixtures of the corresponding 2,3-dideoxy- 3 -(phenylsulfonyl)-hexopyranoses through a Ferrier rearrangement. The anomeric alkoxyl radical fragmentation of these gamma-hydroxy sulfories using the system (diacetoxyiodo)benzene and iodine gave vinyl sulfones with structures of 1,2-dideoxy-4-O-formyl-2-(phenylsulfonyl)-pent-I-enitol and configurations D-erythro, L-erythro, and D-threo at the two stereogenic centers. (c) 2005 Elsevier Ltd. All rights reserved.

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页码：5265 / 5268

页数：4

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