4-Amino-1-3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone

Base Information

• Chemical Name: 4-Amino-1-3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone
• CAS No.: 134790-40-2
• Molecular Formula: C23H19F2N3O6
• Molecular Weight: 471.417
• Mol file: 134790-40-2.mol

Synonyms:1’-Epi Gemcitabine 3’,5’-Dibenzoate;4-Amino-1-3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone

Chemical Property of 4-Amino-1-3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone

Chemical Property:

• Melting Point: 125-160°C
• Refractive Index: 1.625
• Boiling Point: 608.4±65.0 °C(Predicted)
• PKA: 4.26±0.10(Predicted)
• PSA: 122.74000
• Density: 1.45±0.1 g/cm3(Predicted)
• LogP: 3.02200
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Sonicated)

Purity/Quality:

99% ^*data from raw suppliers

1’-EpiGemcitabine3’,5’-Dibenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate (a-anomer) of Gemcitabine; antitumor compound An intermediate (α-anomer) of Gemcitabine; antitumor compound.

Technology Process of 4-Amino-1-3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone

There total 4 articles about 4-Amino-1-3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone 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:

Cytosine (71-30-7) + 2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate (134877-42-2) → C23H19F2N3O6 (134790-40-2,1268237-46-2) + (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate (134790-39-9,1268237-46-2)

Guidance literature:

With potassium sulfate; lithium chloride; at 120 - 125 ℃; for 4h; Overall yield = 85.7 %; Overall yield = 405.2 g;

Reference yield:

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose (134877-42-2,134877-43-3,122111-11-9) + 2,4-O,N-bis(trimethylsilyl)cytosine (18037-10-0) → C23H19F2N3O6 (134790-40-2,1268237-46-2) + (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate (134790-39-9,1268237-46-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; Yield given. Multistep reaction. Yields of byproduct given; 1) 1,1,2-trichloroethane, r.t., 30 min, 2) 113 deg C, 18 h;

DOI:10.1055/s-1992-26167

Reference yield:

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate (1173824-58-2,143157-25-9,143157-22-6) → C23H19F2N3O6 (134790-40-2,1268237-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 2 h / 23 °C

2: 1) Me₃SiOTf / 1) 1,1,2-trichloroethane, r.t., 30 min, 2) 113 deg C, 18 h

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.1055/s-1992-26167

upstream raw materials:

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

2,4-O,N-bis(trimethylsilyl)cytosine

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate

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