70838-47-0

Basic information

• Product Name: 3'',5''-Dibenzoylthymidine
• Synonyms: 3'',5''-Dibenzoylthymidine
• CAS NO: 70838-47-0
• Molecular Formula: C₂₄H₂₂N₂O₇
• Molecular Weight: 450.44068
• Mol File: 70838-47-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'',5''-Dibenzoylthymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'',5''-Dibenzoylthymidine(70838-47-0)
• EPA Substance Registry System: 3'',5''-Dibenzoylthymidine(70838-47-0)

Safety Data

• Hazardous Substances Data: 70838-47-0(Hazardous Substances Data)

Upstream product

• 51255-12-0 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-D-erythro-pentafuranose 
• 3444-09-5 1,3-bis(trimethylsilyl)thymine 
• 175024-33-6 C₂₃H₂₉N₂O₇P 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 142405-82-1 Phenyl 3,5-di-O-benzoyl-2-deoxy-1-thio-α-D-threo-pentofuranoside 
• 134614-93-0 Phenyl 2-deoxy-1-thio-α-D-threo-pentofuranoside 
• 132620-67-8 Phenyl 3,5:6,7-di-O-isopropylidene-2-deoxy-1-thio-L-gluco-heptofuranoside 
• 65-85-0 benzoic acid 
• 165047-02-9 ((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl benzoate 
• 1822-73-7 phenylthioethylene 
• 191538-87-1 C₁₉H₁₆O₅ 
• 65-71-4 thymin 
• 196867-32-0 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-iodo-β-D-xylopentofuranosyl)thymine 
• 108647-88-7 ((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate 

Downstream Products

• 137121-87-0 α/β-D-thymidine 
• 16053-52-4 threothymidine 

Relevant articles and documents

Inversion of secondary chiral alcohols in toluene with the tunable complex of R3N{single bond}R′COOH

The SN2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R′COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR′COOH is crucial for the SN2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields.

An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols

Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-β-D-xylo-pentofuranosyl 5-10 and β-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed.

N-glycosylation with glycosyl diethyl phosphites: A highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides

A facile and direct method for the construction of 2′-deoxy-β-N-glycosidic linkages in 2′-deoxyribonucleoside synthesis has been developed by using 3-(3,4,5-trimethoxybenzoyl)-protected 2-deoxyribofuranosyl diethyl phosphites as a glycosyl donor in the presence of trimethylsilyl triflate, wherein coupling reactions with silylated pyrimidine bases have been found to exhibit β-selectivities up to 96%.

A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates

A trimethylsilyl triflate-mediated coupling reaction to produce protected 2′-deoxynucleosides has been developed by using N,N,N',N'-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.

Stereoselective Synthesis of 2'-Deoxy-β-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases

The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-α-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (α:β = 1:24 - 0:1) to afford 2'-deoxy-β-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields.The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable α form.A subsequent SN2 type attack to the intermediate will lead to the β-nucleosides.By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-β-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside.On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products.The product distribution of the regioisomers was, however, proved to change with reaction time.For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (α:β = 1:2 - 1:4.8).The isolated yields to the 9-β isomers after purification were acceptable for practical use.

β-Selective synthesis of 2′-deoxynucleosides by the coupling of 2-deoxy-1-thio-D-threo-pentofuranosides with silylated thymine

The coupling of the 3,5-O-isopropylidene derivative of phenyl 2-deoxy-1-thio-D-threo-pentofuranoside with silylated thymine in the presence of N-bromosuccinimide yielded 1-(2-deoxy-β-D-threo-pentofuranosyl)thymine with highly anomeric selectivity.

Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides

2'-Deoxyribonucleosides are regiospecifically synthesized in high yields by catalyzing with KI-dibenzo-18-crown-6 PTC the condensation between unprotected silylated purines and pyrimidines and the appropriate easily available 2-deoxy-ribofuranosyl or pyranosyl sugar derivatives.