3,5-Dibenzoate-2-deoxy-2,2-difluoro-L-threo-pentonic acid γ-lactone

Base Information

• Chemical Name: 3,5-Dibenzoate-2-deoxy-2,2-difluoro-L-threo-pentonic acid γ-lactone
• CAS No.: 197452-15-6
• Molecular Formula: C19H14F2O6
• Molecular Weight: 376.31
• Mol file: 197452-15-6.mol

Synonyms:3,5-Dibenzoate-2-deoxy-2,2-difluoro-L-threo-pentonic acid γ-lactone;3,5-Dibenzoate-2-deoxy-2,2-difluoro-L-threo-pentonic acid gamma-lactone

Chemical Property of 3,5-Dibenzoate-2-deoxy-2,2-difluoro-L-threo-pentonic acid γ-lactone

Chemical Property:

• PSA: 78.90000
• LogP: 2.62970

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,5-Dibenzoate-2-deoxy-2,2-difluoro-L-threo-pentonic acid γ-lactone

There total 2 articles about 3,5-Dibenzoate-2-deoxy-2,2-difluoro-L-threo-pentonic acid γ-lactone 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:

(R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-difluoro-3-hydroxy-propionic acid ethyl ester (166376-98-3,166376-97-2) → 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentono-γ-lactone (197452-15-6,122111-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Dowex-50 (H⁺) resin, H₂O / methanol / 120 h

2: 2,6-lutidine / CH₂Cl₂ / 36 h / Ambient temperature

With 2,6-dimethylpyridine; Dowex-50 (H⁺) resin; water; In methanol; dichloromethane;

DOI:10.1021/jm970275y

Reference yield:

benzoyl chloride (98-88-4) + (4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one (166275-25-8) → 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentono-γ-lactone (197452-15-6,122111-02-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 36h; Ambient temperature;

DOI:10.1021/jm970275y

Reference yield: 33.0%

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentono-γ-lactone (197452-15-6,122111-02-8) → 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentofuranose (143157-25-9,143157-22-6)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at -50 ℃; for 0.666667h;

DOI:10.1021/jm970275y

upstream raw materials:

benzoyl chloride

(4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one

(R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-difluoro-3-hydroxy-propionic acid ethyl ester

Downstream raw materials:

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentofuranose

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-(methylsulfonyl)-L-erythro-pentofuranose

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)uracil

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-fluorocytosine