Synthesis of D-hexos-5-uloses by Novel in Situ Hydrolysis of Epoxides Derived from 6-deoxyhex-5-enopyranosides

Philomena M. Enright; Kathy M. O'Boyle; Paul V. Murphy

doi:10.1021/ol006714w

Synthesis of D-hexos-5-uloses by Novel in Situ Hydrolysis of Epoxides Derived from 6-deoxyhex-5-enopyranosides

Philomena M. Enright
, Kathy M. O'Boyle
, Paul V. Murphy

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

12 Citations (Scopus)

Abstract

formula presented Epoxides derived from 2,3,4-tri-O-protected-6-deoxyhex-5-enopyranosides are hydrolyzed in situ to ultimately give novel protected-D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls, 5-ketohexoses) in moderate to high yields. The products adopt a bicyclic structure (1,6-anhydropyranos-5-ulose) in solution with the pyranose ring in ⁴C₁ conformation. The methodology has been used to prepare D-xylo-hexos-5-ulose (5-ketoglucose), a synthetic precursor to 1-deoxynojirimycin and a possible intermediate in the biosynthesis of inositols.

Original language	English
Pages (from-to)	3929-3932
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	24
DOIs	https://doi.org/10.1021/ol006714w
Publication status	Published - 30 Nov 2000
Externally published	Yes

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title = "Synthesis of D-hexos-5-uloses by Novel in Situ Hydrolysis of Epoxides Derived from 6-deoxyhex-5-enopyranosides",

abstract = "formula presented Epoxides derived from 2,3,4-tri-O-protected-6-deoxyhex-5-enopyranosides are hydrolyzed in situ to ultimately give novel protected-D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls, 5-ketohexoses) in moderate to high yields. The products adopt a bicyclic structure (1,6-anhydropyranos-5-ulose) in solution with the pyranose ring in 4C1 conformation. The methodology has been used to prepare D-xylo-hexos-5-ulose (5-ketoglucose), a synthetic precursor to 1-deoxynojirimycin and a possible intermediate in the biosynthesis of inositols.",

author = "Enright, \{Philomena M.\} and O'Boyle, \{Kathy M.\} and Murphy, \{Paul V.\}",

year = "2000",

month = nov,

day = "30",

doi = "10.1021/ol006714w",

language = "English",

volume = "2",

pages = "3929--3932",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

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TY - JOUR

T1 - Synthesis of D-hexos-5-uloses by Novel in Situ Hydrolysis of Epoxides Derived from 6-deoxyhex-5-enopyranosides

AU - Enright, Philomena M.

AU - O'Boyle, Kathy M.

AU - Murphy, Paul V.

PY - 2000/11/30

Y1 - 2000/11/30

N2 - formula presented Epoxides derived from 2,3,4-tri-O-protected-6-deoxyhex-5-enopyranosides are hydrolyzed in situ to ultimately give novel protected-D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls, 5-ketohexoses) in moderate to high yields. The products adopt a bicyclic structure (1,6-anhydropyranos-5-ulose) in solution with the pyranose ring in 4C1 conformation. The methodology has been used to prepare D-xylo-hexos-5-ulose (5-ketoglucose), a synthetic precursor to 1-deoxynojirimycin and a possible intermediate in the biosynthesis of inositols.

AB - formula presented Epoxides derived from 2,3,4-tri-O-protected-6-deoxyhex-5-enopyranosides are hydrolyzed in situ to ultimately give novel protected-D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls, 5-ketohexoses) in moderate to high yields. The products adopt a bicyclic structure (1,6-anhydropyranos-5-ulose) in solution with the pyranose ring in 4C1 conformation. The methodology has been used to prepare D-xylo-hexos-5-ulose (5-ketoglucose), a synthetic precursor to 1-deoxynojirimycin and a possible intermediate in the biosynthesis of inositols.

UR - https://www.scopus.com/pages/publications/0034736320

U2 - 10.1021/ol006714w

DO - 10.1021/ol006714w

M3 - Article

SN - 1523-7060

VL - 2

SP - 3929

EP - 3932

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Synthesis of D-hexos-5-uloses by Novel in Situ Hydrolysis of Epoxides Derived from 6-deoxyhex-5-enopyranosides

Abstract

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