Stereocontrolled synthesis of 1-acetylen-2,3-di-o-benzyl-tetrahydrofurans, 1,4-anhydro-arabinitol, and α,β-dihydroxy-γ-alkyl-butyrolactones
✍ Scribed by David D. Díaz; Miguel A. Ramírez; J. Pedro Ceñal; J. Roberto Saad; Carlos E. Tonn; Victor S. Martín
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- English
- Weight
- 171 KB
- Volume
- 15
- Category
- Article
- ISSN
- 0899-0042
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
The title 1,3-anhydro sugar (10) was obtained as crystals by the ring closure of 3-O-acetyl-2,4di-O-benzyl-a,[3-L-arabinopyranosyl chloride (9) which was prepared from methyl fl-Larabinopyranoside via a sequence of reactions involving initial selective 3-O-allylation. Methanolysis of 10 gave 1,3-c/s
The title 1,Zanhydro sugar (8) was synthesized from D-xylose. The key intermediate for the synthesis was 2-0-acetyl-3,4-di-0-benzyl-@-o-xylopyranosyl fluoride, which was transformed into crystalline 8 by ring closure with potassium tert-butoxide. Comparison of the observed vicinal coupling constants