148704-61-4

Basic information

• Product Name: 1-(2-O-acetyl-3,5-di-O-benzoyl-4-C-benzoyloxymethyl-α-L-arabinofuranosyl)thymine
• Synonyms: 1-(2-O-acetyl-3,5-di-O-benzoyl-4-C-benzoyloxymethyl-α-L-arabinofuranosyl)thymine
• CAS NO: 148704-61-4
• Molecular Weight: 642.619
• Mol File: 148704-61-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(2-O-acetyl-3,5-di-O-benzoyl-4-C-benzoyloxymethyl-α-L-arabinofuranosyl)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-O-acetyl-3,5-di-O-benzoyl-4-C-benzoyloxymethyl-α-L-arabinofuranosyl)thymine(148704-61-4)
• EPA Substance Registry System: 1-(2-O-acetyl-3,5-di-O-benzoyl-4-C-benzoyloxymethyl-α-L-arabinofuranosyl)thymine(148704-61-4)

Safety Data

• Hazardous Substances Data: 148704-61-4(Hazardous Substances Data)

Upstream product

• 55797-64-3 1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose 
• 98-88-4 benzoyl chloride 
• 108-24-7 acetic anhydride 
• 148704-59-0 3,5-di-O-benzoyl-4-C-benzoyloxymethyl-1,2-O-isopropylidene-β-L-arabinofuranose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 

Downstream Products

• 148704-69-2 1-(2-deoxy-3-O-methanesulfonyl-5-O-triphenylmethyl-4-C-triphenylmethyloxymethyl-α-L-erythro-pentofuranosyl)thymine 
• 148704-63-6 1-(3,5-di-O-benzoyl-4-C-benzoyloxymethyl-2-O-methanesulfonyl-α-L-arabinofuranosyl)thymine 
• 148704-65-8 1-(3,5-O-benzoyl-4-C-benzoyloxymethyl-2-bromo-2-deoxy-α-L-arabinofuranosyl)thymine 
• 148704-64-7 1-(3,5-O-benzoyl-4-C-benzoyloxymethyl-2-chloro-2-deoxy-α-L-arabinofuranosyl)thymine 
• 148704-60-3 2,2'-anhydro-1-(3,5-O-benzoyl-4-C-benzoyloxymethyl-α-L-ribofuranosyl)thymine 
• 148704-66-9 1-(3,5-di-O-benzoyl-4-C-benzoyloxymethyl-2-deoxy-α-L-erythro-pentofuranosyl)thymine 
• 148704-71-6 1-(5-O-benzoyl-4-C-benzoyloxymethyl-2,3-dideoxy-α-L-glycero-pent-2-enofuranosyl)thymine 
• 148704-62-5 1-(3,5-di-O-benzoyl-4-C-benzoyloxymethyl-α-L-arabinofuranosyl)thymine 

Relevant articles and documents

SYNTHESIS OF 1-(3-AZIDO-2,3-DIDEOXY-4-C-HYDROXYMETHYL-α-L-threo-PENTOFURANOSYL)THYMINE, 1-(2,3-DIDEOXY-4-C-HYDROXYMETHYL-α-L-glycero-PENTOFURANOSYL)THYMINE AND 1-(2,3-DIDEOXY-4-C-HYDROXYMETHYL-α-L-glycero-PENT-2-ENOFURANOSYL)THYMINE

1-(2-O-Acetyl-3,5-di-O-benzoyl-4-C-benzoyloxymethyl-α-L-arabinofuranosyl)thymine (II) was converted to 2,2'-anhydro derivative V by selective deacetylation, mesylation and treatment with 1,8-diaza-bicycloundec-7-ene.Cleavage of the 2,2'-anhydro ring in compound V with hydrogen chloride or bromide afforded the respective 2'-chloro and 2'-bromo derivatives VI and VII.Reaction of compound VII with Cu/Zn couple and subsequent debenzoylation led to 1-(2,3-dideoxy-4-C-hydroxymethyl-α-L-pent-2-enofuranosyl)thymine (IX).Catalytic hydrogenation of IX gave 1-(2,3-dideoxy-4-C-hydroxymethyl-α-L-glycero-pentofuranosyl)thymine (X).Dehalogenation of compound VI with tributyltin hydride and debenzoylation afforded 1-(2-deoxy-4-C-hydroxymethyl-α-L-erythro-pentofuranosyl)thymine (XII).Tritylation of compound XII, followed by mesylation, detritylation and nucleophilic substitution with azide furnished 1-(3-azido-2,3-dideoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)thymine (XXII).