3,5-Dibenzoyl-DDFR

Base Information

• Chemical Name: 3,5-Dibenzoyl-DDFR
• CAS No.: 1173824-58-2
• Molecular Formula: C19H16F2O6
• Molecular Weight: 378.329
• Mol file: 1173824-58-2.mol

Synonyms:3,5-Dibenzoyl-DDFR

Chemical Property of 3,5-Dibenzoyl-DDFR

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 495.925°C at 760 mmHg
• PKA: 9.95±0.70(Predicted)
• Flash Point: 253.726°C
• PSA: 82.06000
• Density: 1.412g/cm³
• LogP: 2.42150
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-hydroxytetrahydrofuran-2-yl)methyl benzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,5-Dibenzoyl-DDFR

There total 8 articles about 3,5-Dibenzoyl-DDFR 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%

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8) → (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate (1173824-58-2,143157-25-9,143157-22-6)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; diethyl ether; at 10 - 30 ℃; for 1h;

DOI:10.1055/s-1992-26167

Reference yield:

C25H21F2NO5 → (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate (1173824-58-2,143157-25-9,143157-22-6)

Guidance literature:

With hydrogenchloride; In water; toluene; at 45 ℃; for 24h;

Reference yield:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8) → C19H16F2O6 (153012-08-9) + C19H18F2O6 + (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate (1173824-58-2,143157-25-9,143157-22-6)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at -78 ℃; for 3h; Overall yield = 89.7 percent; Overall yield = 33.9 g;

upstream raw materials:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate

benzoyl chloride

2-deoxy-2,2-difluoro-1-carbonylribose

ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate

Downstream raw materials:

1-O-triisopropylsilyl-2-deoxy-2,2-difluoro-3,5-di-O-benzoyl-D-arabinofuranose

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

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

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

Refernces

• 1、 -. "High-selectivity synthesis method for gemcitabine intermediate". Paragraph 0059-0060. . Retrieved 2021/01/29.
• 2、 -. "Purification method of gemcitabine intermediate". Paragraph 0079-0080. . Retrieved 2021/06/22.