Remarkable beta-selectivity in the synthesis of beta-1-C-arylglucosides: stereoselective reduction of acetyl-protected methyl 1-C-arylglucosides without acetoxy-group participation
Deshpande, PP; Ellsworth, BA; Buono, FG; Pullockaran, A; Singh, J; Kissick, TP; Huang, MH; Lobinger, H; Denzel, T; Mueller, RH
| HERO ID | 4947512 |
|---|---|
| In Press | No |
| Year | 2007 |
| Title | Remarkable beta-selectivity in the synthesis of beta-1-C-arylglucosides: stereoselective reduction of acetyl-protected methyl 1-C-arylglucosides without acetoxy-group participation |
| Authors | Deshpande, PP; Ellsworth, BA; Buono, FG; Pullockaran, A; Singh, J; Kissick, TP; Huang, MH; Lobinger, H; Denzel, T; Mueller, RH |
| Journal | Journal of Organic Chemistry |
| Volume | 72 |
| Issue | 25 |
| Page Numbers | 9746-9749 |
| Abstract | An efficient and practical process to generate beta-C-arylglucoside derivatives was achieved. The process described involves Lewis acid mediated ionic reduction of a peracetylated 1-C-aryl methyl glucoside derived from the addition of an aryl-Li to selectively protected delta-D-gluconolactone. The reduction of the 2-acetoxy-1-C-oxacarbenium ion intermediates proceeds with a high degree of selectivity to give beta-C-arylglucosides without 2-acetoxy group participation. Furthermore, during the reduction process we also identified an unprecedented critical role of water. By changing from the usual benzyl ether protecting groups because of cost and chemical compatibility concerns, the new process is made additionally efficient and highly selective. |
| Doi | 10.1021/jo071051i |
| Pmid | 17997568 |
| Wosid | WOS:000251313600042 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |