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Efficient and stereoselective synthesis of methyl 3-O-(3,6-anhydro-β-d-galactopyranosyl)-α-d-galactopyranoside and methyl 3,6-anhydro-4-O-β-d-galactopyranosyl-α-d-galactopyranoside

✍ Scribed by Abdul Rashid; William Mackie

Publisher
Elsevier Science
Year
1992
Tongue
English
Weight
652 KB
Volume
223
Category
Article
ISSN
0008-6215

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✦ Synopsis

Methyl 3-O-(3,6-anhydro-beta-D-galactopyranosyl)-alpha-D-galactopyranoside (3) and methyl 3,6-anhydro-4-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside (4) have been synthesised stereoselectively using three coupling procedures. Acceptable yields were achieved using acetylated derivatives as donors and trimethylsilyl triflate as the catalyst. Intramolecular tosylate displacement to form 3,6-anhydro rings proceeded in methanolic sodium methoxide.

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