A new chemical synthesis of Ascopyrone P from 1,5-anhydro-D-fructose

Mikkel Andreassen; Inge Lundt

doi:10.1016/j.carres.2006.03.037

A new chemical synthesis of Ascopyrone P from 1,5-anhydro-D-fructose

Department of Endocrinology

Abstract

The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-D-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).

Original language	English
Journal	Carbohydrate research
Volume	341
Issue number	10
Pages (from-to)	1692-6
Number of pages	5
ISSN	0008-6215
DOIs	https://doi.org/10.1016/j.carres.2006.03.037
Publication status	Published - 24 Jul 2006

Keywords

Acetylation
Fructose/analogs & derivatives

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10.1016/j.carres.2006.03.037

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title = "A new chemical synthesis of Ascopyrone P from 1,5-anhydro-D-fructose",

abstract = "The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-D-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).",

keywords = "Acetylation, Fructose/analogs & derivatives",

author = "Mikkel Andreassen and Inge Lundt",

year = "2006",

month = jul,

day = "24",

doi = "10.1016/j.carres.2006.03.037",

language = "English",

volume = "341",

pages = "1692--6",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Pergamon Press",

number = "10",

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TY - JOUR

T1 - A new chemical synthesis of Ascopyrone P from 1,5-anhydro-D-fructose

AU - Andreassen, Mikkel

AU - Lundt, Inge

PY - 2006/7/24

Y1 - 2006/7/24

N2 - The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-D-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).

AB - The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-D-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).

KW - Acetylation

KW - Fructose/analogs & derivatives

U2 - 10.1016/j.carres.2006.03.037

DO - 10.1016/j.carres.2006.03.037

M3 - Journal article

C2 - 16630602

VL - 341

SP - 1692

EP - 1696

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 10

ER -

A new chemical synthesis of Ascopyrone P from 1,5-anhydro-D-fructose

Abstract

Keywords

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