Abstract
2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60°C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group. The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0-5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-a (and ß)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-a-D-ribofuranosylmaleimide, the a-isomer of showdomycin, from (20) is described.
| Original language | English |
|---|---|
| Pages (from-to) | 2267-2272 |
| Number of pages | 6 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| DOIs | |
| Publication status | Published - 1981 |
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C-nucleoside studies. Part 13. A new synthesis of 2,3,5-tri-O-benzyl- α(and β)-D-ribofuranosylethyne involving benzyloxy participation, and a synthesis of α-showdomycin. / Aslani-Shotorbani, Gaffar; Buchanan, J. Grant; Edgar, Alan R.; Shanks, Colin T.; Williams, Gavin C.
In: Journal of the Chemical Society, Perkin Transactions 1, 1981, p. 2267-2272.Research output: Contribution to journal › Article
TY - JOUR
T1 - C-nucleoside studies. Part 13. A new synthesis of 2,3,5-tri-O-benzyl- α(and β)-D-ribofuranosylethyne involving benzyloxy participation, and a synthesis of α-showdomycin
AU - Aslani-Shotorbani, Gaffar
AU - Buchanan, J. Grant
AU - Edgar, Alan R.
AU - Shanks, Colin T.
AU - Williams, Gavin C.
PY - 1981
Y1 - 1981
N2 - 2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60°C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group. The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0-5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-a (and ß)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-a-D-ribofuranosylmaleimide, the a-isomer of showdomycin, from (20) is described.
AB - 2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60°C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group. The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0-5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-a (and ß)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-a-D-ribofuranosylmaleimide, the a-isomer of showdomycin, from (20) is described.
U2 - 10.1039/P19810002267
DO - 10.1039/P19810002267
M3 - Article
SP - 2267
EP - 2272
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1472-7781
ER -