2'-Deoxy-2',2'-difluoro-5'-cytidylic Acid

Base Information

• Chemical Name: 2'-Deoxy-2',2'-difluoro-5'-cytidylic Acid
• CAS No.: 116371-67-6
• Molecular Formula: C9H12F2N3O7P
• Molecular Weight: 343.178
• Mol file: 116371-67-6.mol

Synonyms:[(2R,3S,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate;

Chemical Property of 2'-Deoxy-2',2'-difluoro-5'-cytidylic Acid

Chemical Property:

• Melting Point: 151-153?C
• Boiling Point: 618.3 °C at 760 mmHg
• Flash Point: 327.736 °C
• PSA: 166.94000
• Density: 2.095 g/cm³
• LogP: -0.59040
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Water (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

Gemcitabine Monophosphate, Formate salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Gemcitabine Monophosphate is a gemcitabine derivative. It is an antineoplastic agent. Gemcitabine derivative. An antineoplastic agent

Technology Process of 2'-Deoxy-2',2'-difluoro-5'-cytidylic Acid

There total 14 articles about 2'-Deoxy-2',2'-difluoro-5'-cytidylic Acid 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: 90.0%

2’-deoxy-2’,2’-difluoro-cytidine (103882-84-4,103882-85-5) → Gemcitabine monophosphate (116371-67-6)

Guidance literature:

With 1,4-dithio-D,L-threitol; potassium chloride; ATP; magnesium chloride; deoxycytidine kinase; BSA; In water; at 37 ℃; for 0.75h; pH=7.6; Tris buffer; Enzymatic reaction;

DOI:10.1021/bi902132u

Reference yield: 78.0%

gemcitabine (95058-81-4,103882-85-5) → Gemcitabine monophosphate (116371-67-6)

Guidance literature:

gemcitabine; With trichlorophosphate; at 20 ℃; for 0.15h; Flow reactor; Green chemistry;

With water; at 20 ℃; Temperature; chemoselective reaction; Flow reactor; Green chemistry;

DOI:10.1021/op5002066

Reference yield:

4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one hydrochloride → Gemcitabine monophosphate (116371-67-6)

Guidance literature:

With trimethyl phosphite; trichlorophosphate; at 20 ℃; for 2h; Cooling with ice;

DOI:10.1021/acs.biochem.0c00543

upstream raw materials:

gemcitabine

2’-deoxy-2’,2’-difluoro-cytidine

C₃₀H₂₉F₂N₃O₆

N⁴,O-^3’-dibenzoyl-2’,2’-difluoro-2-deoxycytidine

Refernces

• 1、 Farrell, Kristen B.,Zinnen, Shawn,Thamm, Douglas H.,Karpeisky, Alexander. "Gemcitabine-Ibandronate Conjugate Enables the Bone-Targeted Combination Therapy in Bone Cancer: Synthesis and Efficacy in Combination with Docetaxel". . p. 2530 - 2539. Retrieved 2021/11/30.
• 2、 Huang, Zhen,Li, Chuncheng,Li, Na,Luo, Danyan,Tang, Shuo,Yang, Shuzhang. "New Mechanism of Gemcitabine and Its Phosphates: DNA Polymerization Disruption via 3′-5′ Exonuclease Inhibition". . p. 4344 - 4352. Retrieved 2020/12/03.