127244-82-0

Basic information

• Product Name: (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid
• Synonyms: (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid
• CAS NO: 127244-82-0
• Molecular Weight: 494.62
• Mol File: 127244-82-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid(127244-82-0)
• EPA Substance Registry System: (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid(127244-82-0)

Safety Data

• Hazardous Substances Data: 127244-82-0(Hazardous Substances Data)

Upstream product

• 127218-27-3 (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid tert-butyl ester 
• 42926-80-7 5'-O-(4-monomethoxytrityl)-2'-deoxythymidine 
• 7791-71-1 5'-O-tritylthymidine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 83479-97-4 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 50-89-5 thymidine 
• 198267-31-1 1-[(2R,4S,5R)-5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-(tert-butyldiphenylsilanyloxy)tetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 83467-48-5 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 172974-50-4 1'-thymine-(3'-O-t-butyl-diphenylsilyl-6'-carboxamido-2',5',6',7'-tetradeoxy-β-D-ribo-6'-ene-heptofuranosyl) 
• 127244-83-1 <6'-diethoxyphosphonate-3'-O-tert-butyldiphenylsilyl-6'-thio-(2'-pyridyl)-2',5',6'-trideoxy-β-D-ribo-hexofuranosyl>-1-thymine 
• 127218-28-4 (6'-diethoxyphosphonate-3'-O-tert-butyldiphenylsilyl-2',5',6'-trideoxy-β-D-ribo-hexofuranosyl)-1-thymine 
• 124685-20-7 6'-<(3'-azido-2',3',5',6'-tetradeoxy-β-D-ribo-hexofuranosyl)-1-thymine>-phosphonic acid 
• 339178-22-2 (2S,3S,5R)-3-benzenesulfonyloxy-2-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester 
• 339178-17-5 (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester 
• 164864-68-0 1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 127218-27-3 (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid tert-butyl ester 
• 188796-21-6 C₅₈H₆₃N₅O₁₁Si 
• 157723-20-1 C₅₇H₆₁N₅O₁₂Si 

Relevant articles and documents

Preparation of 4'-substituted thymidines by substitution of the thymidine 5'-esters.

tert-Butyl thymidylate 3 was prepared from thymidine 1 in six steps and 67% overall yield. When the lithium trianion of 3 (prepared by treatment of 3 with excess LDA and then excess tert-butyllithum) is reacted with electrophiles, trapping occurs stereoselectively from either the alpha- or beta-face depending on the electrophile (Scheme 1). Deuterioacetic acid in deuteriomethanol affords mainly the alpha-deuterated product (4a/4b = 2.4:1) while all other electrophiles, e.g., phenylselenenyl chloride, allyl bromide, and N-fluorobenzenesulfonimide (NFSI), give predominately (or completely) the products of attack from the beta-face (5bcd/4bcd = 3.7:1 to 100:0). The structures of the products were determined by coupling constant analysis of both the initial compounds and the diols 6bcd prepared by ester reduction and by formation of the acetonides 7bc. The methyl ester of the 3'-epimer of thymidylic acid 9 was also prepared from thymidine 1 in nine steps and 74% overall yield. When the lithium trianion of 9 (prepared by treatment of 9 with excess LDA and then excess tert-butyllithum) is reacted with electrophiles, trapping also occurs stereoselectively with attack on either the alpha- or beta-face depending on the electrophile (Scheme 2). Again, deuterioacetic acid in deuteriomethanol affords mainly the beta-deuterated product (11a/10a = 1.6:1) while all other electrophiles, e.g., phenylselenenyl chloride, methyl iodide, allyl bromide, and NFSI, gave predominately (or completely) the product of attack from the alpha-face (8.7:1 to 100: 0). Again, the structures of the products were determined by coupling constant analysis of both the initial compounds, and the diols 12b-e were prepared by reduction of the ester and by formation of the acetonides 13bcd. A rationale has been developed using molecular mechanics calculations to explain the diastereoselectivity that involves staggered axial attack on the sp(2) carbon opposite to the pseudoaxial alkoxy group in the most stable half-chair conformation of the enolates, as shown in Schemes 3-5.

Stereoselectivity in radical reactions of 2'-deoxynucleosides. A synthesis of an isostere of 3'-azido-3'-deoxythymidine-5'-monophosphate (AZT-5' monophosphate)

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