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Synthesis of 4-o-(4,6-ethylidene-α-D-glucopyranosyl)-4′-demethyl-3′-O-[14C]methyl-4-epipodophyllotoxin

✍ Scribed by J. E. Swigor; U. J. Haynes

Book ID
102372794
Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
224 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of the title compound (5) is described. Treatment of 4‐O‐(4,6‐ethylidene‐α‐D‐glucopyranosyl)‐4′‐demethyl‐4‐epipodophyllotoxin with sodium metaperiodate in acetonitrile formed the highly colored 4‐O‐(4,6‐ethylidene‐α‐D‐glucopyranosyl)‐3′,4′‐dioxo‐4‐epipodophyllotoxin (1). Hydrogenation using 10% palladium on carbon produced the 3′,4′‐dihydroxy compound (2). Protection of the 4′ hydroxy was achieved by benzylation (3). Treatment with excess [^14^C]methyl iodide under basic conditions introduced the label on the 3′ position (4). Deprotection yielded the title compound in an overall yield of 6%.

📜 SIMILAR VOLUMES

Synthesis of 4-0-(4,6-di[14C]ethylidene-
Synthesis of 4-0-(4,6-di[14C]ethylidene-α-D-glucopyranosyl)-4′-demethyl-4-epipodophyllotoxin
✍ U. J. Haynes; J. E. Swigor 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 French ⚖ 204 KB

## Abstract The synthesis of the title compound (5) is described. Protection of 4‐0‐(4, 6‐ethylidene‐α‐D‐glucopyranosyl)‐4′‐demethyl‐4‐epipodophyllotoxin (1) with benzylchloroformate in the presence of pyridine gave 4‐0‐(4, 6‐ethylidene‐α‐D‐glucopyranosyl)‐4′‐carbobenzyloxy‐4‐epipodophyllotoxin (2)

Synthesis of allyl and benzyl 4-O-(3,6-d
Synthesis of allyl and benzyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-α-l-rhamnopyranoside
✍ Jose R. Mariño-Albernas; Vicente Verez-Bencomo; Leandro Gonzalez; Carlos S. Pere 📂 Article 📅 1987 🏛 Elsevier Science 🌐 English ⚖ 803 KB

Condensation of 2,4-di-O-acetyl-3,6-di-O-methyl-a-~glucopyranosyl bromide with either ally1 or benxyl2,4-di-0-methyl-cu+rhamnopyranoside in the presence of mercuric cyanide, followed by 0-deacetylation, gave the title oligosaccharides in excellent yields.