3Epigemcitabine

Base Information

• Chemical Name: 3Epigemcitabine
• CAS No.: 103882-85-5
• Molecular Formula: C₉H₁₁F₂N₃O₄
• Molecular Weight: 263.201
• Mol file: 103882-85-5.mol

Synonyms:3Epigemcitabine;4-Amino-1-(Deoxy-2,2-difluoro-D-threo-pentofuranosyl)-2(1H)-pyrimidinon;(Gemcitabine Impurity;3’-Epi Gemcitabine (Gemcitabine Impurity);4-Amino-1-(Deoxy-2,2-difluoro-D-threo-pentofuranosyl)-2(1H)-pyrimidinone

Chemical Property of 3Epigemcitabine

Chemical Property:

• Vapor Pressure: 2.41E-11mmHg at 25°C
• Melting Point: 102-104°C
• Refractive Index: 1.652
• Boiling Point: 482.7°C at 760 mmHg
• PKA: 11.65±0.70(Predicted)
• Flash Point: 245.7°C
• PSA: 110.60000
• Density: 1.84g/cm³
• LogP: -0.70740
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

3’-EpiGemcitabine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An impurity from the synthesis of Gemcitabine.

Technology Process of 3Epigemcitabine

There total 112 articles about 3Epigemcitabine 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%

(2R,3R,5R)-5-(4-amino-2-oxopyrimidine-1(2H)-yl)-4,4-difluoro-2-((3-fluorobenzoyloxy)methyl)tetrahydrofuran-3-yl 3-fluorobenzoate (942288-40-6) → gemcitabine (95058-81-4,103882-85-5)

Guidance literature:

With ammonia; water; at 20 ℃; for 3h;

Reference yield: 82.7%

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate (134790-39-9,1268237-46-2) → gemcitabine (95058-81-4,103882-85-5)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 3h;

Reference yield: 76.9%

1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one (896109-84-5) → gemcitabine (95058-81-4,103882-85-5)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 12h; Product distribution / selectivity;

upstream raw materials:

1-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)-4-acetamidopyrimidin-2-one

(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

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

Downstream raw materials:

Gemcitabine monophosphate

gemcitabine

C₃₂H₃₁F₂N₃O₇

C₃₀H₂₉F₂N₃O₆

Refernces

• 1、 Wang, Yedong,Li, Yuan,Lu, Jia,Qi, Huixin,Cheng, Isabel,Zhang, Hongjian. "Involvement of CYP4F2 in the metabolism of a novel monophosphate ester prodrug of gemcitabine and its interaction potential in vitro". . . Retrieved 2018.
• 2、 Pulido, Jesse,de Cabrera, Maria,Sobczak, Adam J.,Amor-Coarasa, Alejandro,McGoron, Anthony J.,Wnuk, Stanislaw F.. "4-N-Alkanoyl and 4-N-alkyl gemcitabine analogues with NOTA chelators for 68-gallium labelling". . p. 5624 - 5630. Retrieved 2018.
• 3、 Anliker,McClure,Britton,Stephan,Maple,Cooke. "Degradation chemistry of gemcitabine hydrochloride, a new antitumor agent". . p. 716 - 719. Retrieved 1994.
• 4、 Matsushita, Katsunori,Okuda, Takumi,Mori, Shohei,Konno, Masamitsu,Eguchi, Hidetoshi,Asai, Ayumu,Koseki, Jun,Iwagami, Yoshifumi,Yamada, Daisaku,Akita, Hirofumi,Asaoka, Tadafumi,Noda, Takehiro,Kawamoto, Koichi,Gotoh, Kunihito,Kobayashi, Shogo,Kasahara, Yuuya,Morihiro, Kunihiko,Satoh, Taroh,Doki, Yuichiro,Mori, Masaki,Ishii, Hideshi,Obika, Satoshi. "A Hydrogen Peroxide Activatable Gemcitabine Prodrug for the Selective Treatment of Pancreatic Ductal Adenocarcinoma". . p. 1384 - 1391. Retrieved 2019.
• 5、 Fang, Jianguo,Hou, Yanan,Li, Jin,Li, Xinming,Wang, Song,Zhao, Jintao. "Combination of chemotherapy and oxidative stress to enhance cancer cell apoptosis". . p. 3215 - 3222. Retrieved 2020/04/08.