✦ LIBER ✦

Deoxy-nitrosugars. 10th Communication. Synthesis of Isosteric Phosphonate Analogues of Ulose-1-Phosphates

✍ Scribed by Radomir Julina; Andrea Vasella

Publisher: John Wiley and Sons
Year: 1985
Tongue: German
Weight: 898 KB
Volume: 68
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19850680402

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

A general approach to isosteric phosphonate analogues of ulose‐l‐phosphates is described. A base‐catalysed chain elongation via a Michael addition of 1‐deoxy‐1‐nitro‐sugars 4, 8, and 16 to the vinylphosphonate 18 followed by hydrolysis of the nitro adducts gave the analogues of D‐ribulose‐1‐phosphate, D‐fructose‐1‐phosphate, and D‐sedoheptulose‐1,7‐diphosphate 21, 23, and 27, respectively, in high yields.

📜 SIMILAR VOLUMES

Deoxy-nitrosugars 12th communication Syn

Deoxy-nitrosugars 12th communication Synthesis of isosteric mono-phosphonate analogues of β-and α-D-fructose 2,6-bisphosphate

✍ Roger Meuwly; Andrea Vasella 📂 Article 📅 1986 🏛 John Wiley and Sons 🌐 German ⚖ 703 KB

The 8-o-configuration of 1 was deduced from its I3C-NMR spectrum [2].

Deoxy-nitrosugars. 4th communication. Co

Deoxy-nitrosugars. 4th communication. Convenient synthesis of 1-deoxy-1-nitroaldoses

✍ Bernard Aebischer; Andrea Vasella 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 359 KB

## Abstract A new synthesis of 1‐deoxy‐1‐nitroaldoses by ozonolysis of __N__‐glycosylnitrones according to the procedure of __Bailey et al.__ is described. Based on the oxime **1**, the mannofuranosylnitrones **3–5** were obtained in yields of 86–88% and the 1‐deoxy‐1‐nitromannose **6** in yields o