149656-26-8

Basic information

• Product Name: 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose
• Synonyms: 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose
• CAS NO: 149656-26-8
• Molecular Weight: 553.632
• Mol File: 149656-26-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose(149656-26-8)
• EPA Substance Registry System: 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose(149656-26-8)

Safety Data

• Hazardous Substances Data: 149656-26-8(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 115728-43-3 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 125440-13-3 (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 115728-44-4 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 

Downstream Products

• 3416-05-5 3'-Deoxythymidine 
• 121687-74-9 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>thymine 
• 125440-17-7 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>thymine 
• 69655-05-6 Dideoxyinosine 
• 117723-57-6 N⁶-methyl-9-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine 
• 85326-07-4 N⁶-methyl-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)adenine 
• 132364-17-1 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl]uracil 
• 141192-09-8 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>uracil 
• 128075-93-4 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine 
• 141684-84-6 6-chloro-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>-9H-purine 
• 141684-85-7 9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>hypoxanthine 
• 141684-86-8 N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine 
• 126049-67-0 N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>cytosine 
• 141684-92-6 2-amino-5-chloro-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>-9H-purine 

Relevant articles and documents

A Highly Stereoselective Glycosylation of 2-(Phenylselenenyl)-2,3-dideoxyribose Derivative with Thymine: Synthesis of 3'-Deoxy-2',3'-didehydrothymidine and 3'-Deoxythymidine

A highly stereoselective synthesis of 3'-deoxy-2',3'-didehydrothymidine (D4T) and 3'-deoxythymidine (D2T) was achieved from the condensation of 2-(phenylselenenyl)-2,3-dideoxyribose derivative and silylated thymine in the presence of trimethylsilyl triflate.

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.