Enolic ortho esters .6. A new 'Pyranose->cyclohexane' transformation via 1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-D-xylo-hex-5-enopyranose
Bourke, DG; Collins, DJ; Hibberd, AI; Mcleod, MD
| HERO ID | 4947874 |
|---|---|
| In Press | No |
| Year | 1996 |
| Title | Enolic ortho esters .6. A new 'Pyranose->cyclohexane' transformation via 1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-D-xylo-hex-5-enopyranose |
| Authors | Bourke, DG; Collins, DJ; Hibberd, AI; Mcleod, MD |
| Journal | Australian Journal of Chemistry |
| Volume | 49 |
| Issue | 3 |
| Page Numbers | 425-434 |
| Abstract | Hydrolysis of methyl 6-chloro-6-deoxy-2,3,4-tri-O-methyl-alpha-D-glucopyranoside (19b) and Swern oxidation of the resulting anomeric hemiacetals (20) gave 6-chloro-6-deoxy-2,3,4-tri-O-methyl-D-glucono-1,5-lactone (21), treatment of which with 1,2-bis(trimethylsilyloxy)ethane in the presence of trimethylsilyl trifluoromethanesulfonate gave 6-chloro-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-D-glucopyranose (23a). Conversion of (23a) into the corresponding 6-iodo compound (23b) and treatment of this with 1,8-diazabicyclo[5.4.0]undec-7-ene afforded the enolic ortho ester 1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-D-xylo-hex-5-enopyranose (26). Reaction of(26) with methylmagnesium iodide, or with titanium tetrachloride, gave (1R,6S,7R,8R,9S)-7,8,9-trimethoxy-6-methyl-2,5-dioxabicyclo[4.3.1]decan-1-ol (34), or (2S,3R,4R)-5,5-ethylenedioxy-2,3,4-trimethoxycyclohexanone (28), respectively. |
| Doi | 10.1071/CH9960425 |
| Wosid | WOS:A1996UM46800024 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |