1345024-31-8

Basic information

• Product Name: (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide
• CAS NO: 1345024-31-8
• Molecular Weight: 508.69
• Mol File: 1345024-31-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide(1345024-31-8)
• EPA Substance Registry System: (E)-N-(((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)carbamoyl)-3-methoxy-2-methylacrylamide(1345024-31-8)

Safety Data

• Hazardous Substances Data: 1345024-31-8(Hazardous Substances Data)

Upstream product

• 287933-72-6 tert-Butyl-[(R)-1-(2,3-dihydro-furan-3-yl)methoxy]-diphenyl-silane 
• 52410-41-0 3-methoxy-2-methylacryloyl chloride 
• 1345023-95-1 C₂₅H₃₂O₆Si 
• 1345024-12-5 (1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexane-1-carboxylic acid 
• 1345024-14-7 C₂₃H₂₈O₃Si 
• 1345024-08-9 ((1R,4R,5R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxabicyclo[3.1.0]hexan-1-yl)methanol 
• 1345024-04-5 (R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-4,5-dihydrofuran-2-carbonitrile 
• 1345023-99-5 (2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxytetrahydrofuran-2-carbonitrile 
• 1345023-89-3 (2S,3R,4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-cyanotetrahydrofuran-3-yl acetate 

Downstream Products

• 1345024-36-3 C₂₇H₃₂N₂O₄Si 

Relevant articles and documents

Synthesis of conformationally north-locked pyrimidine nucleosides built on an oxabicyclo[3.1.0]hexane scaffold

Beginning with a known 3-oxabicyclo[3.1.0]hexane scaffold (I), the relocation of the fused cyclopropane ring bond and the shifting of the oxygen atom to an alternative location engendered a new 2-oxabicyclo[3.1.0]hexane template (II) that mimics more closely the tetrahydrofuran ring of conventional nucleosides. The synthesis of this new class of locked nucleosides involved a novel approach that required the isocyanate II (B = NCO) with a hydroxyl-protected scaffold as a pivotal intermediate that was obtained in 11 steps from a known dihydrofuran precursor. The completion of the nucleobases was successfully achieved by quenching the isocyanate with the lithium salts of the corresponding acrylic amides that led to the uracil and thymidine precursors in a single step. Ring closure of these intermediates led to the target, locked nucleosides. The anti-HIV activity of 29 (uridine analogue), 31 (thymidine analogue), and 34 (cytidine analogue) was explored in human osteosarcoma (HOS) cells or modified HOS cells (HOS-313) expressing the herpes simplex virus 1 thymidine kinase (HSV-1 TK). Only the cytidine analogue showed moderate activity in HOS-313 cells, which means that the compounds are not good substrates for the cellular kinases.