Approaches to the Syntheses of 2- and 3-Phosphonomethyl Derivatives of Arabinose Via Pentacovalent Oxaphospholene Methodology

Autor:	Todd A. Madsen, Todd R. Boehlow, Larry A. Alegria, Cynthia K. McClure, Royce A. Wilkinson
Rok vydání:	1999
Předmět:	Arabinose Stereochemistry Organic Chemistry Diol Biochemistry Inorganic Chemistry chemistry.chemical_compound chemistry Aldol reaction Derivative (finance) Glyceraldehyde acetonide Glyoxal Organic chemistry Stereoselectivity
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 144:177-180
ISSN:	1563-5325 1042-6507
Popis:	Approaches to the syntheses of 2- and 3-phosphonomethyl derivatives of arabinose via pentacovalent oxaphospholene methodology are outlined. Condensation of the requisite pentacovalent oxaphospholenes with either a mono-protected glyoxal derivative or glyceraldehyde acetonide were highly stereoselective, producing the syn aldol product as the major isomer in both cases. The reduction of 4a to the diol did not give the expected stereoselectivity. Stereochemical correlation of 5 and 6 were via the carbonates.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6461d4437b40b5355dc3e8f76b5af074 https://doi.org/10.1080/10426509908546211 Zobrazit plný text záznamu