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Efficient synthesis of S- and Se-(2,3,4,6-tetra-O-acetyl-β-d-glucosyl) thiophosphates and selenophosphates

✍ Scribed by Paweł Lipka; Maria Michalska

Publisher
Elsevier Science
Year
1983
Tongue
English
Weight
255 KB
Volume
113
Category
Article
ISSN
0008-6215

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✦ Synopsis

Chmielewski and BeMiller' described a series of O,O-di-tert-butyl S-cc-and -/3-D-glucopyranosyl thiophosphates and S-cc-and -/I-D-galactopyranosyl thiophosphates and found that these products were thermally unstable, decomposed during chromatography, and were rather impure. The authors were not able to prepare the free acids. Following our earlier work'-', we now describe an efficient preparation of the relatively stable di-tert-butyl esters of S-( 2,3,4,6-tetra-O-acetyl-/?-D-glucopyranosyl) thiophosphate (3) and Se-(Z&3,4,6-O-acetyl-B-D-glucopyranosyl) selenophosphate (4) in high yield, and their quantitative conversion into the free acids.

📜 SIMILAR VOLUMES

Molecular and crystal structure of (2,3,
Molecular and crystal structure of (2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-(1 → 3)-[2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl-(1 → 6)]-(2,4-di-O-acetyl-β-d-glucopyranosyl)-(1 → 3)-1,2,4,6-tetra-O-acetyl-β-d-glucopyranose
✍ Keiichi Noguchi; Eiichi Kobayashi; Kenji Okuyama; Shinichi Kitamura; Kenichi Tak 📂 Article 📅 1994 🏛 Elsevier Science 🌐 English ⚖ 785 KB

## Crystals of the tetrasaccharide, (2,3,4,6-tetra-0acetyl-fi-D-ghxopyranosyl~-(1 + 3)-[2,3,4,6-tetra-O-acetyI+LD-gIucopyranosyI-(1 --t 6)]-(2,4-di-0-acetyl-g\_D-glucopyranosyl)-1 --) 3)-1,2,4,6-tetrad-acetyl$?-n-ghicopyranose, belong to tge monoclinic system, space group P2,, with a = 12.709(4),