Elsevier

Tetrahedron

Volume 53, Issue 18, 5 May 1997, Pages 6539-6554
Tetrahedron

Synthesis of 3″,4″-bisphosphate-containing analogs of adenophostin A

https://doi.org/10.1016/S0040-4020(97)00309-8Get rights and content

Abstract

Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-αβ-d-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded α-glucosides 8 and 17, respectively. Protective group manipulations (8 → 10 and 17 → 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-d-glucopyranosyl)-1-O-acetoxymethylglycol (11) and 3-O(3,4,6-tri-O-acetyl-2-O-benzyl-α-d-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-bytyldiphenylsilyl-sn-glycerol (21). Vorbrüggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5.

The synthesis of adenophostin A analogs 4 and 5 is described

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