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Synthesis of mono- and di-benzyl ethers of benzyl α- l-rhamnopyranoside
Benzylidenation of benzyl α- l-rhamnopyranoside ( 1) gave the exo- ( 2) and endo-2,3- O-benzylidene diastereomers ( 3), hydrogenolysis of which afforded the 3-benzyl and 2-benzyl ethers of 1, respectively. Hydrogenolysis of the 4- O-benzyl derivatives ( 14 and 15) of 2 and 3 yielded the 3,4-di-benzy...
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| Published in: | Carbohydrate research 1978, Vol.65 (2), p.209-217 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
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| Summary: | Benzylidenation of benzyl α-
l-rhamnopyranoside (
1) gave the
exo- (
2) and
endo-2,3-
O-benzylidene diastereomers (
3), hydrogenolysis of which afforded the 3-benzyl and 2-benzyl ethers of
1, respectively. Hydrogenolysis of the 4-
O-benzyl derivatives (
14 and
15) of
2 and
3 yielded the 3,4-di-benzyl and 2,4-dibenzyl ethers of
1, whereas hydrolysis of
14 and
15 gave the
4-benzyl ether of
1. The 2,3-dibenzyl ether of
1 was synthesised
via the 4-
O-allyl derivative of
1. |
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| ISSN: | 0008-6215 1873-426X |
| DOI: | 10.1016/S0008-6215(00)84312-8 |