US EPA

1200636 

Journal Article 

LARGE-SCALE SYNTHESIS OF D-MANNOSE 6-PHOSPHATE AND OTHER HEXOSE 6-PHOSPHATES 

Meldal, M; Christensen, MK; Bock, K 

1992 

Yes 

Carbohydrate Research
ISSN: 0008-6215
EISSN: 1873-426X 

235 

115-127 

10.1016/0008-6215(92)80082-C 

WOS:A1992KA06700010 

The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha -D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)- alpha -D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha -D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethyl-silyl)- alpha -D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha -D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha -D-glucopyranoside 6-phosphate disodium salt. Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)- alpha -D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol. Butyl and hexadecyl alpha -D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl- alpha -D-mannopyranosyl bromide in silver triflate-promoted reactions.