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

Gaffar Aslani-Shotorbani, J. Grant Buchanan, Alan R. Edgar, Colin T. Shanks, Gavin C. Williams

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)2267-2272
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - 1981

Fingerprint

Showdomycin
Sorbitol
Nucleosides
Toluene
Ribose
Isomers
Chlorides
2,3,5-tri-O-benzyl D-ribofuranosylethyne

Cite this

@article{c42622949ed9486ca4841bdf4cad9395,
title = "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",
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.",
author = "Gaffar Aslani-Shotorbani and Buchanan, {J. Grant} and Edgar, {Alan R.} and Shanks, {Colin T.} and Williams, {Gavin C.}",
year = "1981",
doi = "10.1039/P19810002267",
language = "English",
pages = "2267--2272",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",

}

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 journalArticle

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 -