N-Carboxybenzyl GeMcitabine

Base Information

• Chemical Name: N-Carboxybenzyl GeMcitabine
• CAS No.: 138685-83-3
• Molecular Formula: C17H17F2N3O6
• Molecular Weight: 397.335
• Mol file: 138685-83-3.mol

Synonyms:N-Carboxybenzyl Gemcitabine;N-CBZ GEMCITABINE;

Chemical Property of N-Carboxybenzyl GeMcitabine

Chemical Property:

• Melting Point: >115°C (dec.)
• PSA: 122.91000
• LogP: 0.95090
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

N-Carboxybenzyl Gemcitabine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Gemcitabine (G305000) derivative.

Technology Process of N-Carboxybenzyl GeMcitabine

There total 11 articles about N-Carboxybenzyl GeMcitabine 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: 92.0%

4-(benzyloxycarbonylamino)-1-(2-deoxy-2,2-difluoro-5-O-[tertbutyl(dimethyl)silyl]-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one (1613293-13-2) → 4-(benzyloxycarbonylamino)-1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one (138685-83-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/jm500531z

Reference yield: 91.0%

benzyl chloroformate (501-53-1,94274-21-2) + gemcitabine (95058-81-4,103882-85-5) → 4-(benzyloxycarbonylamino)-1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one (138685-83-3)

Guidance literature:

gemcitabine; With pyridine; chloro-trimethyl-silane; at 4 - 20 ℃; for 1.5h; Inert atmosphere;

benzyl chloroformate; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2019.08.003

Reference yield: 41.0%

C23H33F2N3O6Si2 → 4-(benzyloxycarbonylamino)-1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one (138685-83-3)

Guidance literature:

With triethylamine; In methanol; at 20 ℃;

upstream raw materials:

benzyl chloroformate

gemcitabine hydrochloride

4-amino-1-((2R,4R,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoro-4-hydroxytetrahydrofuran-2-yl)pyrimidin-2(1H)-one

4-(benzyloxycarbonylamino)-1-(2-deoxy-2,2-difluoro-5-O-[tertbutyl(dimethyl)silyl]-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one

Downstream raw materials:

gemcitabine

Refernces

• 1、 Trznadel, Roksana,Singh, Aleksandra,Kleczewska, Natalia,Liberska, Joanna,Ruszkowski, Piotr,Celewicz, Lech. "Synthesis and in vitro anticancer activity of new gemcitabine-nucleoside analogue dimers containing methyltriazole or ester-methyltriazole linker". . p. 2587 - 2594. Retrieved 2019/08/12.
• 2、 Weiss, Jason T.,Dawson, John C.,Fraser, Craig,Rybski, Witold,Torres-Sánchez, Carmen,Bradley, Mark,Patton, E. Elizabeth,Carragher, Neil O.,Unciti-Broceta, Asier. "Development and bioorthogonal activation of palladium-labile prodrugs of gemcitabine". . p. 5395 - 5404. Retrieved 2014/07/08.