Practical synthesis of four stereoisomers of 6-(t-butyldiphenylsiloxy)- 3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol via dithiane coupling with oxirane

Mitsuaki Ide, Keiji Tsunashima, Masaya Nakata

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The anion derived from 2-substituted 1,3-dithiane derivative (S)-2-[2- (t-butyldiphenylsiloxy)-1-methylethyl]-1-3-dithiane, with n-BuLi at room temperature (r.t.) in THF was subjected to coupling with 2,3-disubstituted oxirane, (2S,3S), or (2S,3R)-2,3-epoxy-1-(triphenylmethoxy)butane, at r.t., giving the coupling products in satisfactory yield. These coupling products were subjected to de-dithioacetalization, and the resulting carbonyl compounds were stereoselectively reduced to afford four stereoisomers of 6- (t-butyldiphenylsiloxy)-3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol.

Original languageEnglish
Pages (from-to)2501-2507
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume72
Issue number11
Publication statusPublished - 1999 Nov

Fingerprint

Ethylene Oxide
Stereoisomerism
Hexanes
Carbonyl compounds
Anions
Derivatives
Temperature
dithiane
n-butyllithium
butane
1,3-dithiane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Practical synthesis of four stereoisomers of 6-(t-butyldiphenylsiloxy)- 3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol via dithiane coupling with oxirane. / Ide, Mitsuaki; Tsunashima, Keiji; Nakata, Masaya.

In: Bulletin of the Chemical Society of Japan, Vol. 72, No. 11, 11.1999, p. 2501-2507.

Research output: Contribution to journalArticle

@article{c7f69b7f54b4463a8b046d3892f34c40,
title = "Practical synthesis of four stereoisomers of 6-(t-butyldiphenylsiloxy)- 3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol via dithiane coupling with oxirane",
abstract = "The anion derived from 2-substituted 1,3-dithiane derivative (S)-2-[2- (t-butyldiphenylsiloxy)-1-methylethyl]-1-3-dithiane, with n-BuLi at room temperature (r.t.) in THF was subjected to coupling with 2,3-disubstituted oxirane, (2S,3S), or (2S,3R)-2,3-epoxy-1-(triphenylmethoxy)butane, at r.t., giving the coupling products in satisfactory yield. These coupling products were subjected to de-dithioacetalization, and the resulting carbonyl compounds were stereoselectively reduced to afford four stereoisomers of 6- (t-butyldiphenylsiloxy)-3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol.",
author = "Mitsuaki Ide and Keiji Tsunashima and Masaya Nakata",
year = "1999",
month = "11",
language = "English",
volume = "72",
pages = "2501--2507",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "Chemical Society of Japan",
number = "11",

}

TY - JOUR

T1 - Practical synthesis of four stereoisomers of 6-(t-butyldiphenylsiloxy)- 3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol via dithiane coupling with oxirane

AU - Ide, Mitsuaki

AU - Tsunashima, Keiji

AU - Nakata, Masaya

PY - 1999/11

Y1 - 1999/11

N2 - The anion derived from 2-substituted 1,3-dithiane derivative (S)-2-[2- (t-butyldiphenylsiloxy)-1-methylethyl]-1-3-dithiane, with n-BuLi at room temperature (r.t.) in THF was subjected to coupling with 2,3-disubstituted oxirane, (2S,3S), or (2S,3R)-2,3-epoxy-1-(triphenylmethoxy)butane, at r.t., giving the coupling products in satisfactory yield. These coupling products were subjected to de-dithioacetalization, and the resulting carbonyl compounds were stereoselectively reduced to afford four stereoisomers of 6- (t-butyldiphenylsiloxy)-3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol.

AB - The anion derived from 2-substituted 1,3-dithiane derivative (S)-2-[2- (t-butyldiphenylsiloxy)-1-methylethyl]-1-3-dithiane, with n-BuLi at room temperature (r.t.) in THF was subjected to coupling with 2,3-disubstituted oxirane, (2S,3S), or (2S,3R)-2,3-epoxy-1-(triphenylmethoxy)butane, at r.t., giving the coupling products in satisfactory yield. These coupling products were subjected to de-dithioacetalization, and the resulting carbonyl compounds were stereoselectively reduced to afford four stereoisomers of 6- (t-butyldiphenylsiloxy)-3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol.

UR - http://www.scopus.com/inward/record.url?scp=0032719262&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032719262&partnerID=8YFLogxK

M3 - Article

VL - 72

SP - 2501

EP - 2507

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 11

ER -