Transformations in carbohydrate chemistry part 1 - Synthesis of C-2 methylene O- and C-glycosides and sugar derived alpha-methylene-delta-valerolactones from C-2-acetoxymethyl glycals
Gupta, A; Vankar, YD
| HERO ID | 4937124 |
|---|---|
| In Press | No |
| Year | 2000 |
| Title | Transformations in carbohydrate chemistry part 1 - Synthesis of C-2 methylene O- and C-glycosides and sugar derived alpha-methylene-delta-valerolactones from C-2-acetoxymethyl glycals |
| Authors | Gupta, A; Vankar, YD |
| Journal | Tetrahedron |
| Volume | 56 |
| Issue | 43 |
| Page Numbers | 8525-8531 |
| Abstract | C-2-Methylene O- and C-glycosides are readily synthesized from C-2-acetoxymethyl glycals using Nafion-H(R), montmorillonite K-10, LiClO4 (0.07 M) in dichloromethane and Pd(PPh3)(4) as catalysts. Exclusive alpha or beta 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 alpha -methylene-delta -valerolactones in good yields in one step using m-CPBA in the presence of BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved. |
| Doi | 10.1016/S0040-4020(00)00775-4 |
| Wosid | WOS:000090007900014 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-0034693084&doi=10.1016%2fS0040-4020%2800%2900775-4&partnerID=40&md5=9abdd1c26af4831acb15713b4a9d1467 |
| Is Public | Yes |
| Language Text | English |
| Keyword | montmorillonite K-10; Nafion-H; O- and C-glycosides |