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Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates

✍ Scribed by Morten Meldal; Mette Knak Christensen; Klaus Bock

Publisher: Elsevier Science
Year: 1992
Tongue: English
Weight: 1000 KB
Volume: 235
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(92)80082-c

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✦ Synopsis

The syntheses of o-mannose 6-phosphate (41, several D-mannopyranoside 6-phosphates, and methyl a-o-glucopyranoside 6-phosphate are described. Phosphotylation of methyl 2,3,4-tri-O-(trimethylsilyBa-o-mannopyranoside

(2) with phosphorus oxychloride followed by careful hydrolysis gave methyl a-o-mannopyranoside 6-phosphate (IO, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-ttrimethylsilylkr-o-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on p-mannose).

The first method was further used in the synthesis of methyl, butyl, and hexadecyl cY-o-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl a-D-glucopyranoside 6-phosphate disodium salt. Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O_(trimethylsilyl)a-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol. Butyl and hexadecyl cY-o-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-a-D-mannopyranosyl bromide in silver triflate-promoted reactions.

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