128075-93-4

Basic information

• Product Name: 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine
• CAS NO: 128075-93-4
• Molecular Weight: 473.65
• Mol File: 128075-93-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine(128075-93-4)
• EPA Substance Registry System: 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine(128075-93-4)

Safety Data

• Hazardous Substances Data: 128075-93-4(Hazardous Substances Data)

Upstream product

• 58-61-7 adenosine 
• 141684-81-3 6-chloro-9-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>-9H-purine 
• 115728-44-4 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone 
• 125440-13-3 (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 149656-26-8 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 958-09-8 2'-deoxy-D-adenosine 
• 129835-18-3 (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-3-ol 
• 862179-59-7 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-adenosine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 116285-72-4 9-((2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine 
• 73-03-0 cordycepin 
• 65109-11-7 2',5'-bis-O-(tert-butyldimethylsilyl)adenosine 

Downstream Products

• 4097-22-7 2',3'-Dideoxyadenosine 

Relevant articles and documents

Deoxyribosyl analogues of methionyl and isoleucyl sulfamate adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases

2′-Deoxy, 3′-deoxy, and 2′,3′-dideoxyribosyl surrogates of isoleucyl and methionyl sulfamate adenylates have been investigated to identify the pharmacophoric importance of the ribose group for the inhibition of Escherichia coli methionyl-tRNA (MRS) and isoleucyl-tRNA (IRS) synthetases. Molecular modeling of 2′,3′-dideoxyribosyl Met-NHSO2-AMP (9) with the crystal structure of E. coli MRS revealed that the lack of the two hydroxyl groups on ribose was compensated by the formation of an extra hydrogen bond between the ring oxygen and His24, resulting in a small activity reduction.

A Highly Stereoselective Synthesis of Anti-HIV 2',3'-Dideoxy- and 2',3'-Didehydro-2',3'-dideoxynucleosides

A general total synthesic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented.Introduction of an α-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give >/=95percent β-isomer.This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine.The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.