Photochemical oxidation of partially protected derivatives of α-d-glucofuranose and β-d-fructofuranose

Laetitia Den Drijver; Cedric W. Holzapfel; Martha S. van Dyk; Gert J. Kruger

doi:10.1016/0008-6215(87)84006-5

Photochemical oxidation of partially protected derivatives of α-d-glucofuranose and β-d-fructofuranose

Laetitia Den Drijver, Cedric W. Holzapfel, Martha S. van Dyk, Gert J. Kruger

Chemical Sciences

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

4 Citations (Scopus)

Abstract

An improved procedure for the preparation of 1,2-O-isopropylidene-β-d-fructofuranose and its 6-pyruvoylation is described. Photolysis of this ester in benzene furnished 5,6-O-isopropylidene-β-d-lyxo-5-ulofuranose, characterised as the O-methyloxime diacetate. Similary, photochemical oxidation of 1 1,2-O-isopropylidene-6-O-pyruvoyl-α-d-glucofuranose gave 1,2-O-isopropylidene-α-d-lgluco-hexodialo1,4:6,3-difuranose in excellent yield.

Original language	English
Pages (from-to)	65-73
Number of pages	9
Journal	Carbohydrate Research
Volume	161
Issue number	1
DOIs	https://doi.org/10.1016/0008-6215(87)84006-5
Publication status	Published - 15 Mar 1987

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/0008-6215(87)84006-5

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title = "Photochemical oxidation of partially protected derivatives of α-d-glucofuranose and β-d-fructofuranose",

abstract = "An improved procedure for the preparation of 1,2-O-isopropylidene-β-d-fructofuranose and its 6-pyruvoylation is described. Photolysis of this ester in benzene furnished 5,6-O-isopropylidene-β-d-lyxo-5-ulofuranose, characterised as the O-methyloxime diacetate. Similary, photochemical oxidation of 1 1,2-O-isopropylidene-6-O-pyruvoyl-α-d-glucofuranose gave 1,2-O-isopropylidene-α-d-lgluco-hexodialo1,4:6,3-difuranose in excellent yield.",

author = "\{Den Drijver\}, Laetitia and Holzapfel, \{Cedric W.\} and \{van Dyk\}, \{Martha S.\} and Kruger, \{Gert J.\}",

year = "1987",

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doi = "10.1016/0008-6215(87)84006-5",

language = "English",

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T1 - Photochemical oxidation of partially protected derivatives of α-d-glucofuranose and β-d-fructofuranose

AU - Den Drijver, Laetitia

AU - Holzapfel, Cedric W.

AU - van Dyk, Martha S.

AU - Kruger, Gert J.

PY - 1987/3/15

Y1 - 1987/3/15

N2 - An improved procedure for the preparation of 1,2-O-isopropylidene-β-d-fructofuranose and its 6-pyruvoylation is described. Photolysis of this ester in benzene furnished 5,6-O-isopropylidene-β-d-lyxo-5-ulofuranose, characterised as the O-methyloxime diacetate. Similary, photochemical oxidation of 1 1,2-O-isopropylidene-6-O-pyruvoyl-α-d-glucofuranose gave 1,2-O-isopropylidene-α-d-lgluco-hexodialo1,4:6,3-difuranose in excellent yield.

AB - An improved procedure for the preparation of 1,2-O-isopropylidene-β-d-fructofuranose and its 6-pyruvoylation is described. Photolysis of this ester in benzene furnished 5,6-O-isopropylidene-β-d-lyxo-5-ulofuranose, characterised as the O-methyloxime diacetate. Similary, photochemical oxidation of 1 1,2-O-isopropylidene-6-O-pyruvoyl-α-d-glucofuranose gave 1,2-O-isopropylidene-α-d-lgluco-hexodialo1,4:6,3-difuranose in excellent yield.

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U2 - 10.1016/0008-6215(87)84006-5

DO - 10.1016/0008-6215(87)84006-5

M3 - Article

AN - SCOPUS:26844501241

SN - 0008-6215

VL - 161

SP - 65

EP - 73

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 1

ER -

Photochemical oxidation of partially protected derivatives of α-d-glucofuranose and β-d-fructofuranose

Abstract

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