Thymidine, 3'-(phenylmethyl carbonate)

Base Information

• Chemical Name: Thymidine, 3'-(phenylmethyl carbonate)
• CAS No.: 139705-33-2
• Molecular Formula: C18H20N2O7
• Molecular Weight: 376.366
• Mol file: 139705-33-2.mol

Synonyms:

Chemical Property of Thymidine, 3'-(phenylmethyl carbonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thymidine, 3'-(phenylmethyl carbonate)

There total 7 articles about Thymidine, 3'-(phenylmethyl carbonate) 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: 99.0%

carbonic acid benzyl ester 2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester → 3'-O-(benzyloxycarbonyl)thymidine (139705-33-2)

Guidance literature:

With triethylamine trihydrofluoride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1021/ol048426w

Reference yield: 84.0%

→ 3'-O-(benzyloxycarbonyl)thymidine (139705-33-2)

Guidance literature:

With hafnium tetrakis(trifluoromethanesulfonate); In methanol; at 20 ℃; for 16h; chemoselective reaction;

Reference yield: 77.0%

acetone O-(benzyloxycarbonyl)oxime (137160-76-0) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 3'-O-(benzyloxycarbonyl)thymidine (139705-33-2)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 30h; lipase Amano PS;

DOI:10.1021/jo00034a056

upstream raw materials:

acetone O-(benzyloxycarbonyl)oxime

thymidine

benzyl chloroformate

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

Refernces

• 1、 -. "Hafnium trifluoromethanesulfonate catalyzed silyl ether protecting group removing method". Paragraph 0011; 0013; 0014. . Retrieved 2019/01/21.
• 2、 Moris, Franciso,Gotor, Vicente. "A Novel and Convenient Route to 3'-Carbonates from Unprotected 2'-Deoxynucleosides through an Enzymatic Reaction". . p. 2490 - 2492. Retrieved 2007/10/02.