𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of 5-thio-d-allose and the methyl 5-thio-α- and -β-d-allopyranosides

✍ Scribed by Najim A.L. Al-Mosoudi; Neil A. Hughes

Publisher
Elsevier Science
Year
1986
Tongue
English
Weight
895 KB
Volume
148
Category
Article
ISSN
0008-6215

No coin nor oath required. For personal study only.

✦ Synopsis

ABSTRAm 5,6-Anhydro-1,2-0-isopropylidene-3-O-methanesulphonyl-a-~-idofuranose was converted, via the related gZucod$-episulphide, into 6-0-acetyl-5-S-acetyl-1,2-O-isopropylidene-3-O-methanesulphonyl-5-thio-at-D-glucofuranose (9). Replacement of the acetyl groups of 9, or the related 3-toluene-p-sulphonate, by an isopropylidene group and saponification of the sulphonate group gave 1,2-0:5,6-S, O-di-isopropylidene-5-thio-WD-glucofuranose (2). Epimerisation at C-3 of 2 by an oxidation-reduction sequence gave 1,2-O : 5,6-S, 0-di-isopropylidene-5-thio-a-D-allofuranose (20) which was hydrolysed to 5-thio-D-allose (1). Methyl 5-thio-aand -/3-D-allopyranoside were obtained from 1 or by methanolysis of 20. Similar hydrolysis or methanolysis of 2 gave 5-thio-D-glucose or methyl 5-thio-clr-and -&Dglucopyranoside, respectively, thus providing a convenient variation on earlier synthetic routes to these compounds. i3C-N,m.r. data are given for several of these 5-thio-allo and -gluco derivatives. 3 '5Thiopyranoses. Part 9, For Part 8, see ref. 1.

📜 SIMILAR VOLUMES

New syntheses of methyl 5-thio-β-d-arabi
New syntheses of methyl 5-thio-β-d-arabinopyranoside and (+)-biotin
✍ Neil A. Hughes; Ksenija-Maria Kuhajda; Dusan A. Miljkovic 📂 Article 📅 1994 🏛 Elsevier Science 🌐 English ⚖ 436 KB

Previously one of us reported 121 that methyl 3,4-0-isopropylidene-2-Omethanesulfonyl-5.thio-~-D-~~pyranoside (1) readily unde~ent ring ~ntra~tion in methanol to give 2,5-dideo~-2,5-epithio-o-arabinose dimethyl acetal (2). It was of interest to examine this reaction with the corresponding D-arabinos

Synthesis of 3-amino-3-deoxy-5-thio-d-al
Synthesis of 3-amino-3-deoxy-5-thio-d-allose and 3-amino-3-deoxy-1,2-O:5,6-S,O-di-isopropylidene-5-thio-α-d-glucofuranose
✍ Najim A.L. Al-Masoudi; Natiq J. Tooma 📂 Article 📅 1993 🏛 Elsevier Science 🌐 English ⚖ 338 KB

The syntheses have been described of the 2-acetamido-2-deoxy derivatives of 5-thio-D-glucose lm3, 5-thio-D-mannose 4, 5-thio-D-allose 5, 3-acetamido-3-deoxy5thio-D-xylose6, and 4-acetamido-4-deoxy-5-thio-r\_-lyxose6. We now report the syntheses of 3-amino-3-deoxy-5-thio-D-allose hydrochloride and a

A facile synthesis of 5-thio-l-fucose an
A facile synthesis of 5-thio-l-fucose and 5-thio-d-arabinose from d-arabinose
✍ Masayuki Izumi; Osamu Tsuruta; Hironobu Hashimoto 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 955 KB

5-Thio-L-fucopyranose tetraacetate was synthesized in 11 steps from 5-O-trityl-D-arabinofuranose or D-arabinose diethyl dithioacetal by one-carbon elongation at C-5. Highly diastereoselective addition of MeLi in ether to a 1,2-O-isopropylidene-[J-D-arabino-pentodialdo-l,4-furanose derivative was ach

Synthesis of 2-acetamido-2-deoxy-5-thio-
Synthesis of 2-acetamido-2-deoxy-5-thio-β-d-altropyranose
✍ Najim A.L. Al-Masoudi; Neil A Hughes; Natiq J Tooma 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 397 KB

Syntheses have been described of the 2-acetamido-2-deoxy derivatives of 5-thio-Dglucose [1-3], 5-thio-I>mannose [4], and 5-thio-D-allose [5]. We now describe the synthesis of another member of this series, 2-acetamido-2-deoxy-5-thio-I)-altrose. Treatment of oxirane 1 [6] with sodium azide and ammon