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Synthesis of 5-O-methyl-d-galactofuranose

✍ Scribed by Marcos L. Sznaidman; Alicia Fernández Cirelli; Rosa M. de Lederkremer

Book ID
102991129
Publisher
Elsevier Science
Year
1986
Tongue
English
Weight
555 KB
Volume
146
Category
Article
ISSN
0008-6215

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✦ Synopsis

ABSTRACr 5-0-Methyl-D-galactofuranose (7) was synthesized, for the first time, in five steps from D-galactono-1,4-lactone (1) in good overall yield. Tritylation and further acetylation of 1 gave 2,3,5-tri-O-acetyl-6-O-trityl-D-galactono-l,Clactone (2); prolonged acetylation caused elimination to form 2,5-di-0-acetyl-3-deoxy-6-0trityl-D-three-hex-2-enono-1,Clactone. Detritylation of 2 with BF, . Et,0 occurred with acetyl migration and afforded 2,3,6-tri-O-acetyl-D-galactono-1,6lactone (4). Methylation of 4 with CH,N,-BF, . Et,0 gave 5-O-methyl-2,3,6-tri-O-acetyl-Dgalactono-1,4-lactone. Subsequent reduction by disiamylborane followed by controlled deacetylation gave crystalline 7. The 'H-and 13C-n.m.r. spectra of 7 indicated a 1: 1.3 ratio of the (Y and p furanose anomers. RESULTS AND DISCUSSION Tritylation of D-galactono-1 ,Clactone (1) with chlorotriphenylmethane in *Research Members of the Consejo National de Investigaciones Cientificas y TCcnicas.

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Convenient syntheses of 5-O- and 3,5-di-
Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose
✍ Rosa M. de Lederkremer; Carla Marino; Oscar Varela 📂 Article 📅 1990 🏛 Elsevier Science 🌐 English ⚖ 617 KB

Benzoylation of o-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23", gave the 2,6-dibenzoate (2,62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-0-benzoyl-a#o-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-0-(2,3,5,6-tetra-O-~nzoyl-~-o-galactofuranosyl)-~galact