1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose

Base Information

• Chemical Name: 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose
• CAS No.: 171721-00-9
• Molecular Formula: C26H21FO7
• Molecular Weight: 464.447
• Mol file: 171721-00-9.mol

Synonyms:2-DEOXY-2-FLUORO-1,3,5-TRI-O-BENZOYL-L-RIBOFURANOSE;2-DEOXY-2-FLUORO-1,3,5-TRI-O-BZA-L-RIBOFURANOSE;1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-a-L-arabinofuranose;1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose;(2S,3R,4S,5S)-5-((Benzoyloxy)Methyl)-3-fluorotetrahydrofuran-2,4-diyl dibenzoate

Chemical Property of 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 584.13oC at 760 mmHg
• Flash Point: 295.665°C
• PSA: 88.13000
• Density: 1.352g/cm³
• LogP: 3.98900

Purity/Quality:

99% ^*data from raw suppliers

1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-a-L-arabinofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: antineoplastic, alkylating agent 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-a-L-arabinofuranose is a useful intermediate for the synthesis of imidazole nucleoside derivatives and other related nucleosides.

Technology Process of 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose

There total 21 articles about 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-L-arabinofuranose 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: 97.0%

2-O-imidazolylsulfonyl-1,3,5-tri-O-benzoyl-α-L-ribofuranoside → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranose (171721-00-9)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In ethyl acetate; for 14h; Product distribution / selectivity; Heating / reflux;

Reference yield: 65.0%

1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose (171720-99-3) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranose (171721-00-9)

Guidance literature:

With potassium hydrogen bifluoride; hydrogen fluoride; In various solvent(s); at 160 ℃; for 1h;

DOI:10.1021/jm960098l

Reference yield:

1,3,5-Tri-O-benzoyl-α-L-ribofuranose (171866-30-1) → 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranose (171721-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: SO₂Cl₂ / CH₂Cl₂; dimethylformamide / 3.5 h / -40 - 20 °C

2: 21.0 g / CH₂Cl₂; dimethylformamide / 15 h / 20 °C

3: 64 percent / aq. HF; KHF₂ / various solvent(s) / 1 h / 160 °C

With sulfuryl dichloride; potassium hydrogen bifluoride; hydrogen fluoride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1515/znb-2001-0814

upstream raw materials:

1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose

1,3,5-Tri-O-benzoyl-α-L-ribofuranose

1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

Downstream raw materials:

3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl azide

3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl azide

ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-L-arabinofuranosyl)-1,2,3-triazole-5-carboxylate

ethyl 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)-1,2,3-triazole-5-carboxylate

Refernces

• 1、 -. "IMPROVED PROCESS FOR THE PREPARATION OF CLEVUDINE AS ANTI-HBV AGENT". Page/Page column 11. . Retrieved 2008/12/06.
• 2、 Du, Jinfa,Choi, Yongseok,Lee, Kyeong,Chun, Byoung K.,Hong, Joon H.,Chu, Chung K.. "A practical synthesis of L-FMAU from L-arabinose". . p. 187 - 195. Retrieved 2007/10/03.