[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl benzoate

Base Information

• Chemical Name: [(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl benzoate
• CAS No.: 122567-97-9
• Molecular Formula: C17H16 N2 O5
• Molecular Weight: 328.324
• Mol file: 122567-97-9.mol

Synonyms:5'-Benzoyl-2',3'-didehydro-3'-deoxythymidine

Chemical Property of [(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl benzoate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 90.65000
• Density: 1.324g/cm³
• LogP: 1.56790
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

98% ^*data from raw suppliers

Benzoyl stavudine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5''-O-Benzoyl-2'',3''-didehydro-3''-deoxythymidine is a reactant used in the synthetic preparation of the anti-AIDS drug Stavudine (S685250), and preparation of anti-HIV agent Stavudine analogs.

Technology Process of [(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl benzoate

There total 39 articles about [(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(3',5'-di-O-benzoyl-2'-deoxy-2'-iodo-β-D-xylopentofuranosyl)thymine (196867-32-0) → 5′-benzoyl-2′,3′-didehydro-3′-deoxythymidine (122567-97-9)

Guidance literature:

With sodium hydrogensulfide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.11.087

Reference yield: 97.0%

5′-benzoyl-3′α-methanesulfonyl-2′α-bromothymidine (165047-01-8) → 5′-benzoyl-2′,3′-didehydro-3′-deoxythymidine (122567-97-9)

Guidance literature:

With acetic acid; zinc; In methanol; ethyl acetate; for 3.5h; Ambient temperature;

DOI:10.1016/0040-4039(95)01752-4

Reference yield: 93.0%

2,2'-anhydro-1-(5'-O-benzoyl-3'-O-methylsulfonyl-β-D-lyxofuranosyl)thymine (190003-86-2) → 5′-benzoyl-2′,3′-didehydro-3′-deoxythymidine (122567-97-9)

Guidance literature:

With hydrogen iodide; In 1,2-dimethoxyethane; at 20 ℃; for 8h;

DOI:10.1007/BF02495948

upstream raw materials:

benzoyl chloride

stavudin

Benzoic acid (2R,3S)-3-benzenesulfinyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

benzoic acid anhydride

Downstream raw materials:

2',3'-didehydro-3'-deoxy-4-thiothymidine

2',3'-didehydro-2',3'-dideoxy-5-methylcytidine

5'-O-benzoyl-3'-deoxy-4-thiothymidine

3'-deoxy-4-thiothymidine

Refernces

• 1、 Chen, Bang-Chi,Quinlan, Sandra L.,Stark, Derron R.,Reid, J. Gregory,Audia, Vicki H.,et al.. "5'-Benzoyl-2'α'-bromo-3'-O-methanesulfonylthymidine: A Superior Nucleoside for the Synthesis of the Anti-Aids Drug D4T (Stavudine).". . p. 7957 - 7960. Retrieved 1995.
• 2、 Reddy, Jayachandra P.. "Independent synthesis and fate studies of impurities in process intermediates of the anti-AIDS drug d4T". . p. 203 - 207. Retrieved 1998.
• 3、 Sagandira, Cloudius R.,Akwi, Faith M.,Sagandira, Mellisa B.,Watts, Paul. "Multistep Continuous Flow Synthesis of Stavudine". . p. 13934 - 13942. Retrieved 2021/06/28.
• 4、 Kumamoto, Hiroki,Tanaka, Hiromichi. "Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.". . p. 3541 - 3547. Retrieved 2007/10/03.