The synthesis of higher carbon sugars: a study on the rearrangement of higher sugar allylic alcohols

被引：15

作者：

Potopnyk, Mykhaylo A. ^{[1
]}

Cmoch, Piotr ^{[1
]}

Cieplak, Maciej ^{[1
]}

Gajewska, Agnieszka ^{[1
]}

Jarosz, Slawomir ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 07期

关键词：

PHASE-TRANSFER CATALYSIS; HIGH-PRESSURE; CYCLIZATION; GLYCOSIDES; ACCESS; AZODICARBOXYLATE; STEREOCHEMISTRY; MONOSACCHARIDES; CONSTRUCTION; REDUCTION;

D O I：

10.1016/j.tetasy.2011.04.021

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The C12 higher sugar enone 15 (prepared from the corresponding phosphonate and aldehyde) was highly stereoselectively reduced to the D-glycero-allylic alcohol. The epimeric L-glycero-isomer was obtained by the non-selective reduction of the higher enone under Luche conditions. The separate treatment of both allylic alcohols with triflic anhydride provided the corresponding triflates, which in situ underwent allylic rearrangement with the elimination of one of the benzyl groups (from the aldehyde part of the molecule). The stereochemical aspects of this transformation are also discussed. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：780 / 786

页数：7

共 50 条

[21] SYNTHESIS OF HIGHER ACETYLENIC ALCOHOLS
KOVALEV, BG
MATVEEVA, ED
STAN, VV
VOVK, GA
YUDIN, LG
KOST, AN
ZHURNAL ORGANICHESKOI KHIMII, 1980, 16 (10): : 2032 - 2038
[22] SYNTHESIS OF A HIGHER CARBON SUGAR VIA DIRECTED ALDOL CONDENSATION
JAROSZ, S
FRASERREID, B
TETRAHEDRON LETTERS, 1989, 30 (18) : 2359 - 2362
[23] PHYSIOLOGY AND METABOLISM OF SUGAR ALCOHOLS IN HIGHER-PLANTS
LOESCHER, WH
PHYSIOLOGIA PLANTARUM, 1987, 70 (03) : 553 - 557
[24] STRUCTURE OF PRECURSORS OF HIGHER-CARBON SUGARS
CIUNIK, Z
JAROSZ, S
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1993, 49 : 101 - 107
[25] HIGHER CARBON SUGARS FOR THE PREPARATION OF ANSAMYCIN ANTIBIOTICS
MOOTOO, DR
FRASERREID, B
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 3 - CARB
[26] The synthesis of higher-carbon sugar alcohols via indium-mediated acyloxyallylation as potential phase change materials
Draskovits, Markus
Biedermann, Nina
Mihovilovic, Marko D.
Schnuerch, Michael
Stanetty, Christian
MONATSHEFTE FUR CHEMIE, 2025, 156 (01): : 51 - 63
[27] Synthesis of alcohols higher than methanol from carbon monoxide and hydrogen
Frolich, PK
Lewis, WK
INDUSTRIAL AND ENGINEERING CHEMISTRY, 1928, 20 (01): : 354 - 359
[28] SYNTHESIS AND PHYSICAL PROPERTIES OF NORMAL HIGHER ALCOHOLS .1. SYNTHESIS OF NORMAL HIGHER PRIMARY ALCOHOLS OF ODD CARBON NUMBERS FROM UNDECANOL TO PENTACOSANOL
WATANABE, A
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1959, 32 (12) : 1295 - 1298
[29] SYNTHESIS AND PHYSICAL PROPERTIES OF NORMAL HIGHER ALCOHOLS .2. SYNTHESIS OF NORMAL HIGHER PRIMARY ALCOHOLS OF ODD CARBON NUMBERS FROM HEPTACOSANOL TO HEPTATRIACONTANOL
WATANABE, A
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1960, 33 (04) : 531 - 534
[30] SYNTHESIS OF HIGHER ALCOHOLS FROM SYNTHESIS GAS
INTILLE, GM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 79 - 79

← 1 2 3 4 5 →