𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Reductive decyanation of 3-amino-3-cyano-3-deoxy sugars with sodium borohydride. A new approach to 3-amino-3-deoxy sugars.

✍ Scribed by Francisco Santoyo-González; Fernando Hernández-Mateo; Antonio Vargas-Berenguel

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
239 KB
Volume
32
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

3-Amino-3-cyano-3-deoxy sugars obtained by cyclization of dialdehydes with cyanoacetamide and Hojkann rearrangement were reductively decyanuted using sodium borohydn'de providing a new approach to 3-amino-3-deoq sugars.

3-Amino-3-deoxy sugars are components of aminocyclitol', macrolide', and anthracycline antibiotic?. The therapeutic value of these drugs has stimulated the development of diverse strategies"" for the synthesis of 3-amino sugars branched at C-3.

Recently, we have contributed4 in this field developing a methodology for the synthesis of 3-amino-3-cyano-3deoxy sugars type 3 by cyclization of dialdehydes obtained from sugars with cyanoacetamide and Hofmann rearrangement, as depicted in Scheme 1.

📜 SIMILAR VOLUMES

Application of the Hofmann rearrangement
Application of the Hofmann rearrangement in the synthesis of 3-amino sugar derivatives: preparation of some 3-tert-butoxycarbonylamino-3-cyano-3-deoxy and 3-acetamido-methyl-3-tert-butoxycarbonylamino-3-deoxy sugars
✍ Francisco Santoyo Gonzalez; Antonio Vargas Berenguel; Fernando Hernandez Mateo; 📂 Article 📅 1991 🏛 Elsevier Science 🌐 English ⚖ 773 KB

The cyclisation of dialdehydes, obtained from sugars, with cyanoacetamide and subsequent Hofmann rearrangement is a convenient and short approach to the synthesis of 3-amino sugar derivatives branched at C-3. Thus, derivatives of 3-carbamoyL3-cyano-3-deoxy sugars l-4 were transformed into N-protecte

Ring-opening polymerization and copolyme
Ring-opening polymerization and copolymerization of a new benzylated 1,6-anhydro-3-azido-3-deoxy-β-D-allopyranose and synthesis of amino-polysaccharides with 1,6-α-allopyranosidic structure
✍ Kazuyuki Hattori; Takashi Yoshida; Toshiyuki Uryu 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 548 KB

## Abstract Ring‐opening polymerization of a new anhydro‐hexose monomer having an azido group, 1,6‐anhydro‐3‐azido‐2,4‐di‐__O__‐benzyl‐3‐deoxy‐β‐D‐allopyranose (A3ABA), was carried out with Lewis acid catalysts to give a stereoregular (1→6)‐α‐D‐allopyranan derivative having the azido group at the C

Carbohydrates with relevance to the stru
Carbohydrates with relevance to the structure of glycosaminoglycans: The crystal structures of 2-deoxy-2-(sulfoamino)-α-d-glucopyranose sodium salt dihydrate, 2-amino-2-deoxy-α,β-d-glucopyranose 3-(hydrogen sulfate) monohydrate, and 2-amino-2-deoxy-α-d-glucopyranose 6-(hydrogen sulfate) monohydrate
✍ William H. Ojala; Kevin E. Albers; William B. Gleason; Carolyn G. Choo 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 813 KB

The X-ray crystal structures of the glycosaminoglycan-related monosaccharides 2-deoxy-2-(sulfoamino)-a-o-glucopyranose sodium salt dihydrate, 2-amino-2-deoxy-a,fl-o-glucopyranose 3-(hydrogen sulfate) monohydrate, and 2-amino-2-deoxy-ot-D-glucopyranose 6-(hydrogen sulfate) monohydrate have been deter