Stereoselective syntheses of 2,4: 5,6-di-o-isopropylidene-1 -c-phenyl-d-glycero-d-ido-hexitol and 2,4:5,6-di-o-isopropylidene-1 -C-phenyl-d-glycero-d-gulo-hexitol from d-glycero-d-gulo-heptono-γ-lactone. X-ray structure of 1 -O-acetyl-2,4:5,6-di-O-isopropylidene-1-c-phenyl-d-glycero-d-ido-hexitol

Tony K.M. Shing, Hon Chung Tsui, Zhao Hui Zhou, Thomas C.W. Mak

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23 Citations (Scopus)

Abstract

D-glycero-D-gulo-Heptonolactone has been converted by three consecutive reactions (acetonation, reduction and glycol cleavage reaction) into 2,4:5,6-di-O-isopropylidene-D-glucose which with phenylmagnesium bromide gave preponderantly 2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 5. 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 6 has been obtained from 5 via an oxidation-reduction sequence. The structure of 5 has been confirmed by X-ray crystallographic analysis of its 1 -O-acetyl-derivative 12.

Original languageEnglish
Pages (from-to)887-893
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
DOIs
Publication statusPublished - 1992 Jan 1
Externally publishedYes

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Lactones
X rays
Glycols
Bromides
Derivatives
Glucose
propylene
hexitol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Stereoselective syntheses of 2,4: 5,6-di-o-isopropylidene-1 -c-phenyl-d-glycero-d-ido-hexitol and 2,4:5,6-di-o-isopropylidene-1 -C-phenyl-d-glycero-d-gulo-hexitol from d-glycero-d-gulo-heptono-γ-lactone. X-ray structure of 1 -O-acetyl-2,4:5,6-di-O-isopropylidene-1-c-phenyl-d-glycero-d-ido-hexitol",
abstract = "D-glycero-D-gulo-Heptonolactone has been converted by three consecutive reactions (acetonation, reduction and glycol cleavage reaction) into 2,4:5,6-di-O-isopropylidene-D-glucose which with phenylmagnesium bromide gave preponderantly 2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 5. 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 6 has been obtained from 5 via an oxidation-reduction sequence. The structure of 5 has been confirmed by X-ray crystallographic analysis of its 1 -O-acetyl-derivative 12.",
author = "Shing, {Tony K.M.} and Tsui, {Hon Chung} and Zhou, {Zhao Hui} and Mak, {Thomas C.W.}",
year = "1992",
month = "1",
day = "1",
doi = "10.1039/P19920000887",
language = "English",
pages = "887--893",
journal = "Journal of the Chemical Society. Perkin Transactions 1",
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publisher = "Chemical Society",
number = "7",

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TY - JOUR

T1 - Stereoselective syntheses of 2,4

T2 - 5,6-di-o-isopropylidene-1 -c-phenyl-d-glycero-d-ido-hexitol and 2,4:5,6-di-o-isopropylidene-1 -C-phenyl-d-glycero-d-gulo-hexitol from d-glycero-d-gulo-heptono-γ-lactone. X-ray structure of 1 -O-acetyl-2,4:5,6-di-O-isopropylidene-1-c-phenyl-d-glycero-d-ido-hexitol

AU - Shing, Tony K.M.

AU - Tsui, Hon Chung

AU - Zhou, Zhao Hui

AU - Mak, Thomas C.W.

PY - 1992/1/1

Y1 - 1992/1/1

N2 - D-glycero-D-gulo-Heptonolactone has been converted by three consecutive reactions (acetonation, reduction and glycol cleavage reaction) into 2,4:5,6-di-O-isopropylidene-D-glucose which with phenylmagnesium bromide gave preponderantly 2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 5. 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 6 has been obtained from 5 via an oxidation-reduction sequence. The structure of 5 has been confirmed by X-ray crystallographic analysis of its 1 -O-acetyl-derivative 12.

AB - D-glycero-D-gulo-Heptonolactone has been converted by three consecutive reactions (acetonation, reduction and glycol cleavage reaction) into 2,4:5,6-di-O-isopropylidene-D-glucose which with phenylmagnesium bromide gave preponderantly 2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 5. 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 6 has been obtained from 5 via an oxidation-reduction sequence. The structure of 5 has been confirmed by X-ray crystallographic analysis of its 1 -O-acetyl-derivative 12.

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