𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A method for the synthesis of C-(2-deoxy-β-glycosyl) arenes

✍ Scribed by Abu T. Khan; Wasim Ahmed; Richard R. Schmidt

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
593 KB
Volume
280
Category
Article
ISSN
0008-6215

No coin nor oath required. For personal study only.

✦ Synopsis

2,3:4,5-Di-O-isopropylidene-aldehydo-D-arabinose (2) was converted by a Wittig reaction into a mixture of (E/Z)-1-aryl-1,2-dideoxy-3,4:5,6-di-O-isopropylidene-D-arabino-hex-1-enitols (4,5). Selective deprotection of the 5,6-O-isopropylidene group in compounds 4 and 5 followed by selective silylation at position 6 afforded the separable (Z)-l-aryl-6-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-o-arabino-hex-1-enitols 8a-d and the corresponding E-isomers (ga-d). Iodonium-ion-induced cyclization of compounds Ik and 9a-c furnished stereoselectively

10a-c. Full deprotection of compounds 10a-c and then O-acetylation led to compounds lla-e, which on treatment with tributyltin hydride-azobisisobutyronitrile yielded the title compounds (12a-c).

📜 SIMILAR VOLUMES

Stereoselective Synthesis of Indazole 2′
Stereoselective Synthesis of Indazole 2′-Deoxy-β-D-ribonucleosides: Glycosylation of the Nucleobase Anion
✍ Frank Seela; Werner Bourgeois 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 German ⚖ 529 KB

## Abstract The glycosylation of indazolyl anions derived from 4a, b with 2‐deoxy‐3,5‐bis‐__O__‐(4‐methylbenzoyl)‐α‐D‐__erythro__‐pentofuranosyl chloride (5) is described. The reaction was Stereoselective – exclusive β‐D‐anomer formation – but regioisomeric __N__^1^‐ and __N__^2^‐(2′‐deoxy‐β‐D‐ribo