121687-74-9

Upstream product

• 125440-15-5 1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>thymine 
• 66680-87-3 (2-phenylvinyl)tributylstannane 
• 161085-73-0 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-iodo-β-D-erythro-pentofuranosyl>thymine 
• 161085-74-1 1-<5-O-(tert-butyldiphenylsilyl)-3-O-<(phenoxy)thiocarbonyl>-2-deoxy-β-D-erythro-pentofuranosyl>thymine 
• 24850-33-7 allyltributylstanane 
• 928761-46-0 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(1-imidazolyl)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine 
• 928761-47-1 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(pentafluorophenoxy)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine 
• 272778-70-8 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(methylthio)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine 
• 101527-40-6 5'-O-tert-butyldiphenylsilylthymidine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 50-89-5 thymidine 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 201472-26-6 (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol 

Downstream Products

• 149204-36-4 (1S)-1-<<(tert-butyldiphenylsilyl)oxy>methyl>-2,3-dihydrofuran 
• 3416-05-5 3'-Deoxythymidine 

Relevant academic research and scientific papers

Synthesis and photochemical behaviour of a T-T dimer containing an amide linkage

A T-T dimer characterized by an amide linkage to replace the phosphodiester backbone has been synthesized using a modified radical strategy. The new synthetic approach makes use of a thymidin-3′-y1 phosphorodithioate derivative as a precursor of 3′-allyl-

Organocatalytic Conversion of Nucleosides to Furanoid Glycals

A class of organocatalysts that are highly active for the conversion of 2′-deoxynucleosides to furanoid glycals have been discovered. These phosphorimides, (Ph2PS)2NH and (Ph2PSe)2NH, were shown to effectively mediate persilylation of 2′-deoxynucleosides

Synthesis of 3′-C-substituted thymidine derivatives by free-radical techniques: scope and limitations

The scope and limitations of radical-mediated 3′-C-substitution of pyrimidine nucleosides was evaluated with 5′-O-(tert-butyldimethylsilyl)thymidine or its tert-butyldiphenylsilyl analogue having thionoester or thionoamide groups at O-3′, including (methy

Method for preparing 2'-3'-dideoxy-β-nucleosides using 2,2-dideoxy-di(organothio)-pentofuranose intermediates

2,3-Dideoxy-2,2-di(organothio)-B-D-pentofuranosyl-pyrimidines are disclosed as intermediates in the synthesis of 2', 3'-dideoxynucleosides and have the structure shown below. STR1 wherein R4 is a hydroxyl protecting group; X is oxygen or nitrog

Efficient and stereoselective synthesis of 3'-deoxy 3'-C-branched-chain substituted thymidine

In this report, we provide for the first time a facile, efficient, and stereoselective synthesis of 1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-formyl-β-D-erythro-p entofuranosyl]thymine (12), using an intermolecular radical C-C bond formation reacti

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.

Stereoselective glycosylation of hetercyclic bases

A method of preparation of 2',3'-dideoxy and 2',3'-dideoxy-2',3'-didehydronucleosides that includes the step of condensing a 1-O-activated-2-(aromatic or aliphatic)-selenenyl-5-O-protected ribose with a protected heterocyclic base in the presence of trimethylsilyl triflate or a Lewis acid to form a β-anomeric nucleoside in high yield.

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.

Synthesis and evaluation of a series of 1-(3-alkyl-2,3-dideoxy-alpha,beta-D-erythro-pentofuranosyl)thymines.

A series of 1-(3-alkyl-2,3-dideoxy-alpha,beta-D-erythro-pentofuranosyl)thymines (3'-alkyl-3'-deoxythymidines) has been prepared from 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-glycero-pent-2- enono-1,4-lactone ((S)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2(5H)- furanone) by Michael addition of the appropriate organocopper reagent, followed by reduction of the lactone, acetylation of the resulting hemiacetal, and trimethylsilyl triflate-catalyzed coupling with 2,4-di-O-(trimethylsilyl)thymine. The protected nucleosides were desilylated by using tetrabutylammonium fluoride to give anomeric mixtures of the free nucleosides. The unsubstituted 2',3'-dideoxynucleoside analog was similarly prepared from 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-glycero-pentono- 1,4-lactone ((S)5-[(tert-butyldiphenylsilyl)-oxymethyl]-dihydro-2(3H)-fu r anone).