D-Ribose was converted into methyl 5-O-benzyl-beta-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-all
Efficient Synthesis of Methyl 3,5-Di- O -benzyl-α- d -ribofuranoside and Application to the Synthesis of 2‘- C -β-Alkoxymethyluridines
✍ Scribed by Li, Nan-Sheng; Lu, Jun; Piccirilli, Joseph A.
- Book ID
- 125911604
- Publisher
- American Chemical Society
- Year
- 2007
- Tongue
- English
- Weight
- 83 KB
- Volume
- 9
- Category
- Article
- ISSN
- 1523-7060
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📜 SIMILAR VOLUMES
Condensation of 2,4-di-O-acetyl-3,6-di-O-methyl-a-~glucopyranosyl bromide with either ally1 or benxyl2,4-di-0-methyl-cu+rhamnopyranoside in the presence of mercuric cyanide, followed by 0-deacetylation, gave the title oligosaccharides in excellent yields.
## Abstract Methyl 2‐__O__‐benzyl‐6‐deoxy‐3‐__C__‐methyl‐α‐D‐mannopyranoside (2) was synthesized in ten steps by starting from the readily available methyl 2,3‐anhydro‐4,6‐__O__‐benzylidene‐α‐D‐allo‐pyranoside (3). The key step was the stereoselective __cis__‐hydroxylation (cat. osmium(VIII) oxide)