𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A general stereodivergent strategy for the preparation of carbasugars. Syntheses of 5a-carba-α-d-glucose, α-d-galactose, and β-l-gulose pentaacetates from d-mannose

✍ Scribed by Ana M. Gómez; Eduardo Moreno; Serafı́n Valverde; J.Cristóbal López

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
86 KB
Volume
43
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

A stereodivergent approach to 5a-carba-D-and L-pyranoses has been applied to the preparation of 5a-carba-a-D-gluco-, 5a-carba-a-D-galacto-, and 5a-carba-b-L-gulopyranose pentaacetates. The strategy, by which a single precursor can be transformed into three different carbasugars, features a stereoselective reduction followed by deoxygenation of a key polyoxygenated methylcyclohexanone intermediate. The latter is readily available by 6-exo-dig radical cyclization of a D-mannose derivative.

📜 SIMILAR VOLUMES

Stereodivergent synthesis of 5a-carba-he
Stereodivergent synthesis of 5a-carba-hexopyranoses from carbohydrates via 6-exo-dig radical cyclization: preparation of 5a-carba-β-d-manno-, α-d-allo-, β-l-talo- and α-l-gulopyranose pentaacetates from d-mannose
✍ Ana M. Gómez; Eduardo Moreno; Gerardo O. Danelón; Serafı́n Valverde; J.Cristóbal 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 878 KB

Four carbasugars, 5a-carba-b-D-manno-, a-D-allo-, b-L-taloand a-L-gulopyranose pentaacetates, have been prepared in a stereodivergent manner from D-mannose. Alkynyl derivatives of 2,3:4,6-di-O-isopropylidene-D-mannopyranose, which are prepared by homologation at C-1, by reaction with phenyl acetylid