Talofuranoside methyl 6-deoxy-2,3-0-isopropylidene

The solvolysis of 6-deoxy-2,3-(9-isopropylidene-4-0-methanesuIpho-nyl-a-L-talop3T anose (30), with methanolic sodium methoxide, afforded three products which were identified as l,4-anhydro-6-deoxy-2,3-0-isopropyhdene-a-L-mannopjrranose (33, 58%), methyl 6-deoxy-2,3-0-isopropylidene-a-L-talofuranoside (33, 26%), and methyl 6-deoxy-2,3-0-isopropylidene-a-L-mannofuranoside (34, 12%). Both of the minor... 

Simultaneously, the rearrangement was found to occur in the D-series. From the enantiomorph of 177, the corresponding methyl 5-amino-5,6-dideoxy-2,3-0-isopropylidene-a-D-talofuranoside and its N-phthalimido derivative were prepared. For comparison, methyl 5-amino-5,6-dideoxy-2,3-0-isopropylidene-/3-L-allop3nanoside and its N,N-dimethyl derivative were synthesized from methyl 5-0-(p-bromophenyl)sulfonyl-6-deoxy-2,3-0-isopropylidene-a-D-talofurano-side through the azido compound. These compounds were not hydrolyzed. 

D-mannose derivatives.437 All such reactions that they examined with sulfonates of methyl 6-deoxy-2,3-0-isopropylidene-a-D-manno-pyranoside (175) resulted in the formation of furanoside products, and this result probably accounts for some of the conflicting accounts of desulfonylation of the L enantiomorph of 175 (R = Ts).322,438 With acetate ion in boiling N,N-dimethylformamide, the methanesulfonate (175, R = Ms) gave, after saponification, a 65% yield of a mixture of methyl 6-deoxy-2-3-0-isopropylidene-a-D-talofuranoside (176, R = OH) with methyl 6-deoxy-2-3-0-isopropylidene-/3-L-allofurano-side (177, R = OH) in the ratio of 7 1. Displacements atC-5 of the sul-fonylated furanose derivatives 176 and 177 (R = OMs,OTs, or OBs)... 

Me glycoside, 2,3-isopropylidene, S-ben-zoyk Methyl 6-deoxy-2,3-0-isopropyli-dene-5-thiobenzoyl-a-i.-talofuranoside [14990-72-8]... 

Methyl 2-deoxy-3,4-0-isopropylidene-p-D-e/7// ro-pentopyranoside, D-345 Methyl 5-deoxy-2,3-0-isopropylidene-p-D-ribofuranoside, D-362 Methyl 6-deoxy-2,3-0-isopropylidene-a-L-talofuranoside, D-372 Methyl 6-deoxy-2,3-0-isopropylidene-a-D-talopyranoside, D-372 Methyl 6-deoxy-2,3-0-isopropylidene-a-L-talopyranoside, D-372 Methyl 6-deoxy-2,3-0-isopropylidene-7-0-tert-butyldiphenylsilyl-a-D-ia/o-heptopyranoside, D-165... 

Methyl 4-amino-4-deoxy-5-thio-p-L-Iyxopyranoside, A-350 Methyl 3-amino-3-deoxy-5-thio-a-D-xyIopyranoside, A-352 Methyl 5-5-benzoyl-2,3-0-isopropyIidene-5-thio-oc-D-lyxofuranoside, T-80 Methyl 6-deoxy-2,3-0-isopropylidene-5-thiobenzoyl-a-L-talofuranoside, D-379... 

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