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

doi:10.1039/P19920000887

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

24 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 language	English
Pages (from-to)	887-893
Number of pages	7
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	7
DOIs	https://doi.org/10.1039/P19920000887
Publication status	Published - 1992 Jan 1

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1039/P19920000887

Fingerprint

Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this

Shing, T. K. M., Tsui, H. C., Zhou, Z. H., & Mak, T. C. W. (1992). 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. Journal of the Chemical Society, Perkin Transactions 1, (7), 887-893. https://doi.org/10.1039/P19920000887

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. / Shing, Tony K.M.; Tsui, Hon Chung; Zhou, Zhao Hui et al.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 7, 01.01.1992, p. 887-893.

Research output: Contribution to journal › Article › peer-review

Shing, TKM, Tsui, HC, Zhou, ZH & Mak, TCW 1992, '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', Journal of the Chemical Society, Perkin Transactions 1, no. 7, pp. 887-893. https://doi.org/10.1039/P19920000887

Shing TKM, Tsui HC, Zhou ZH, Mak TCW. 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. Journal of the Chemical Society, Perkin Transactions 1. 1992 Jan 1;(7):887-893. doi: 10.1039/P19920000887

Shing, Tony K.M. ; Tsui, Hon Chung ; Zhou, Zhao Hui et al. / 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. In: Journal of the Chemical Society, Perkin Transactions 1. 1992 ; No. 7. pp. 887-893.

@article{c8a9575507de41c58cb4f06908dedec6,

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 = jan,

day = "1",

doi = "10.1039/P19920000887",

language = "English",

pages = "887--893",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "7",

}

TY - JOUR

T1 - 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

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.

UR - http://www.scopus.com/inward/record.url?scp=37049084016&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049084016&partnerID=8YFLogxK

U2 - 10.1039/P19920000887

DO - 10.1039/P19920000887

M3 - Article

AN - SCOPUS:37049084016

SN - 1472-7781

SP - 887

EP - 893

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 7

ER -

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

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this