83956-19-8

Basic information

• Product Name: (desoxy-4-O-p-nitrobenzoyl-3-α-DL-threo-pentopyranosyl)-1-methoxy-4-pyrimidinone-2
• CAS NO: 83956-19-8
• Molecular Weight: 391.337
• Mol File: 83956-19-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (desoxy-4-O-p-nitrobenzoyl-3-α-DL-threo-pentopyranosyl)-1-methoxy-4-pyrimidinone-2(CAS DataBase Reference)
• NIST Chemistry Reference: (desoxy-4-O-p-nitrobenzoyl-3-α-DL-threo-pentopyranosyl)-1-methoxy-4-pyrimidinone-2(83956-19-8)
• EPA Substance Registry System: (desoxy-4-O-p-nitrobenzoyl-3-α-DL-threo-pentopyranosyl)-1-methoxy-4-pyrimidinone-2(83956-19-8)

Safety Data

• Hazardous Substances Data: 83956-19-8(Hazardous Substances Data)

Upstream product

• 3551-55-1 2,4-dimethoxypyrimidine 
• 83956-16-5 methyl desoxy-4-O-p-nitrobenzoyl-3-desoxy-4-α et β-DL-threo-pentopyranoside 

Relevant articles and documents

Synthese stereospecifique de nucleosides pyrimidiques par la methode de Hilbert-Johnson

Condensation of 2,4-dimethoxy pyrimidine with bromoglucosides derived from methyl 4-deoxypentopyranosides 2-7 and from 3,5,6-tri-O-benzoyl glucofuranose, 20, leads in a stereospecific manner to the nucleosides 8-13 and 22 with the trans 1',2'-configuration.The stereochemistry of this reaction is not influenced by the structure of the starting sugar but rather is directed by the presence of the C-2 hydroxyl group.The synthesis of epoxide 18, obtained by the action of NaH on the bromohydrine 17, derived from 7, supports the intervention of a reaction assisted by an epoxide-like intermediate derived from the trans-bromohydrine.On the other hand, the cis-bromohydrine undergoes direct substitution of anomeric halogen by base.The possibility of the formation of a carbocation-like intermediate is discounted since SN1 type glycosylation reactions of 19 by MeOH or t-BuOH lead preferentially to products with the cis-configurations.