Synthesis and radical fragmentation of carbohydrate anomeric nitrates.: Formation of convenient chiral synthetic intermediates

被引：8

作者：

Francisco, CG ^{[1
]}

León, EI ^{[1
]}

Moreno, P ^{[1
]}

Suárez, E ^{[1
]}

机构：

[1] CSIC, Inst Prod Nat & Agrobiol, La Laguna 38206, Tenerife, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(98)00326-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new procedure for the C1-C2 fragmentation of cyclic carbohydrates, through the formation of anomeric alkoxy radicals from the corresponding nitrate esters, with (Bu3SnH)-Bu-n/azobisisobutyronitrile (AIBN), affords acyclic alditols in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2975 / 2978

页数：4

共 40 条

[1] THE CHEMISTRY OF L-ASCORBIC AND D-ISOASCORBIC ACIDS .1. THE PREPARATION OF CHIRAL BUTANETRIOLS AND BUTANETETROLS
ABUSHANAB, E
VEMISHETTI, P
LEIBY, RW
SINGH, HK
MIKKILINENI, AB
WU, DCJ
SAIBABA, R
PANZICA, RP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) : 2598 - 2602
[2] PRACTICAL ENANTIOSPECIFIC SYNTHESES OF (+) ERYTHRO-9-(2S-HYDROXY-3R-NONYL) ADENINE
ABUSHANAB, E
BESSODES, M
ANTONAKIS, K
[J]. TETRAHEDRON LETTERS, 1984, 25 (35) : 3841 - 3844
[3] [Anonymous], 1995, MONOSACCHARIDES THEI
[4] Armas P., 1993, TETRAHEDRON LETT, V34, P7331
[5] ARMAS P, 1992, ANGEW CHEM INT EDIT, V31, P772
[6] ARMAS P, 1993, J AM CHEM SOC, V115, P8865
[7] STEREOCONTROL IN CYCLIZATION OF DIOXOLANYL RADICALS
BATSANOV, AS
BEGLEY, MJ
FLETCHER, RJ
MURPHY, JA
SHERBURN, MS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (10): : 1281 - 1294
[8] STEREOCHEMICAL CONTROL IN CYCLIZATION TO BICYCLIC DIOXOLANES
BEGLEY, MJ
FLETCHER, RJ
MURPHY, JA
SHERBURN, MS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (23) : 1723 - 1725
[9] SYNTHESIS AND PHOTOLYSIS OF SUGAR NITRATES - TRIFLUOROMETHANESULFONATE (TRIFLATE) DISPLACEMENT BY THE NITRATE ANION
BINKLEY, RW
KOHOLIC, DJ
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1984, 3 (01) : 85 - 106
[10] PHOTOLYSIS OF NITRATE ESTERS - PHOTOCHEMICALLY INITIATED INVERSION OF CONFIGURATION
BINKLEY, RW
KOHOLIC, DJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (12) : 2047 - 2048

← 1 2 3 4 →