Diastereoselective Addition of Grignard Reagents to 3,4-O-Isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose and 1-O-Benzoyl-3,4-O-isopropylidene-L-glycero-2-tetrulose

Diastereoselectivity in the addition of Grignard reagents (RMgX) to 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (1) and 1-O-benzoyl-3,4-O-isopropylidene-L-glycero-2-tetrulose (2) depended remarkably on R, X, the solvent, and the reaction temperature. In the reaction of 1 in diethy...

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Published inBulletin of the Chemical Society of Japan Vol. 65; no. 10; pp. 2814 - 2820
Main Authors Nagano, Hajime, Ohno, Mina, Miyamae, Yoko, Kuno, Yukie
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.10.1992
Chemical Soc Japan
Chemical Society of Japan
Subjects
Aliphatic compounds
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
SYSTEMS
ACID
CHELATION
(+)-MALYNGOLIDE
Solvent effect
Grignard reagent
Temperature
Aliphatic compound
Polyol
Diastereoselectivity
Nucleophilic addition
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Summary:Diastereoselectivity in the addition of Grignard reagents (RMgX) to 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (1) and 1-O-benzoyl-3,4-O-isopropylidene-L-glycero-2-tetrulose (2) depended remarkably on R, X, the solvent, and the reaction temperature. In the reaction of 1 in diethyl ether at 0 °C and 2 in tetrahydrofuran were obtained (2R,3S)-adducts with moderate to high diastereoselectivity, while in the reaction of 2 in diethyl ether at −78 °C (2S,3S)-adducts were the major products. (2R)-2-Hydroxymethyl-2-nonyloxirane and (2S)-2-hydroxymethyl-2-tetradecyloxirane were synthesized.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.65.2814