Gupta, Anuradha ; Vankar, Yashwant D. (2000) Synthesis of C-2 methylene O- and C-glycosides and sugar derived α-methylene-δ-valerolactones from C-2-acetoxymethyl glycals Tetrahedron, 56 (43). pp. 8525-8531. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/S0040-4020(00)00775-4
Abstract
C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxymethyl glycals using Nafion-H®, montmorillonite K-10, LiClO4 (0.07 M) in dichloromethane and Pd(PPh3)4 as catalysts. Exclusive α or β selectivities have been observed with various primary, secondary and tertiary alcohols, phenols and diethyl malonate. Further, C-2-acetoxymethyl glycals are also converted into corresponding α-methylene-δ-valerolactones in good yields in one step using m-CPBA in the presence of BF3·Et2O.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Montmorillonite K-10; Nafion-H; O- and C-glycosides |
| ID Code: | 58312 |
| Deposited On: | 31 Aug 2011 06:36 |
| Last Modified: | 31 Aug 2011 06:36 |
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