Highly stereoselective glycosidation of ribose solubilized in apolar organic media via host-guest complexation1
✍ Scribed by Yasutaka Tanaka; Chinmai Khare; Masaki Yonezawa; Yasuhiro Aoyama
- Book ID
- 104228316
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 242 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Ribose complexed with resorcinol-dodecanal cyclotetramer via hydrogen bonding in Ccl4 undergoes highly stereoselective glycosidation with methanol to give methyl B-ribofuranoside under mild and neutral conditions.
Ribose can be solubilized in Ccl4 upon formation of a hydrogen-bonded 1:l complex with resorcinol-dodecanal cyclotetramer 1.3
An interesting and important application of this complexation is development of a new synthetic chemistry of unprotected sugars in apolar organic media.
We wish to report here that bound ribose undergoes glycosidation with methanol in a highly stereoselective manner.
Ribose actually exists as a cyclic hemeacetal, either six-membered pyranose (&) or five-membered furanose (2f), each of which has a pair of a-and 9-anomers.
l3 C NMR spectroscopy of A-ribose complex indicates that ribose is bound highly selectively in the a-pyranose form (2-a), the