70838-44-7

Basic information

• Product Name: 5'-O-BENZOYL-2,3'-ANHYDROTHYMIDINE
• Synonyms: BATH;2,5-METHANO-5H,9H-PYRIMIDO[2,1-B][1,5,3]DIOXAZEPIN-9-ONE, 3-[(BENZOYLOXY)METHYL]-2,3-DIHYDRO-8-METHYL-, (2R,3R,5R)-;5'-O-BENZOYL-2,3'-ANHYDROTHYMIDINE;(2R,3R,5R)-3-[(benzoyloxy)methyl]-2,3-dihydro-8-methyl-2,5-methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one
• CAS NO: 70838-44-7
• Molecular Formula: C₁₇H₁₆N₂O₅
• Molecular Weight: 328.32
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 70838-44-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 472.4 °C at 760 mmHg
• Flash Point: 239.5 °C
• Appearance: Colourless solid
• Density: 1.48 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 5'-O-BENZOYL-2,3'-ANHYDROTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-BENZOYL-2,3'-ANHYDROTHYMIDINE(70838-44-7)
• EPA Substance Registry System: 5'-O-BENZOYL-2,3'-ANHYDROTHYMIDINE(70838-44-7)

Safety Data

• Hazardous Substances Data: 70838-44-7(Hazardous Substances Data)

Usage

Chemical Properties

Colourless solid

Uses

An intermediate in the preparation of anti-HIV pharmaceuticals

Upstream product

• 65-85-0 benzoic acid 
• 50-89-5 thymidine 
• 165047-01-8 5′-benzoyl-3′α-methanesulfonyl-2′α-bromothymidine 
• 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 

Downstream Products

• 15981-92-7 2,3'-anhydrothymidine 
• 167641-88-5 Benzoic acid (2R,3S,5R)-3-iodo-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 158868-16-7 5'-O-benzoyl-3'-(2-tetrazolyl)-2',3'-dideoxythymidine 
• 169382-16-5 1-(5-benzoyl-3-bromo-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine 
• 106060-78-0 3'-azido-5'-O-benzoyl-3'-deoxythymidine 
• 170871-58-6 5'-O-benzoyl-2',3'-dideoxy-3'-phenylselenothymidine 
• 444811-56-7 5'-O-benzoyl-3'-deoxy-3'-{5-[5-(tetrazol-5-yl)-3-oxapentyl]tetrazol-2-yl}thymidine 
• 507232-16-8 3'-O-nitro-5'-O-benzoyl-2'-deoxythymidine 
• 639512-85-9 [6-⁽³⁾H]5'-O-benzoyl-2,3'-anhydrothymidine 
• 159721-77-4 1-(5-O-benzoyl-3-benzoylthio-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine 
• 507232-29-3 5-methyl-3'-O-nitro-5'-O-benzoyl-2'-deoxycytidine 
• 507232-26-0 4-(1,2,4-triazolo)-4-deoxy-3'-O-nitro-5'-O-benzoyl-2'-deoxythymidine 

Relevant articles and documents

Athermal, Chemically Triggered Release of RNA from Thioester Nucleic Acids

An athermal approach to mRNA enrichment from total RNA using a self-immolative thioester linked nucleic acids (TENA) is described. Oligo(thymine) (oT) TENA has a six-atom spacing between bases which allowed TENA to selectively base-pair with polyadenine R

STABILISATION OF RADIOPHARMACEUTICAL PRECURSORS

The invention relates to a method for improving stability of radiopharmaceutical precursors, and in particular non radiolabelled nucleoside derivatives which are used as precursors for production of radiolabelled nucleoside derivatives for use in in vivo imaging procedures such as positron emission tomography (PET). The invention further includes formulations of radiopharmaceutical precursors, and cassettes for automated synthesis apparatus comprising the same.

Efficient transformation of thymidine into 2',3'-didehydro-2',3'-dideoxy- thymidine (D4T) involving opening of a 2,3'-anhydro derivative by phenylselenol

A new, high-yielding method for introduction of the selenophenyl residue at the 3'- position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5'. Further oxidation-elimination sequence followed by basic deprotection afforded 2',3'-didehydro-2',3'- dideoxythymidine (D4T) in 67.5% overall yield from thymidine.