3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine

Base Information

• Chemical Name: 3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine
• CAS No.: 146557-58-6
• Molecular Formula: C₂₉H₃₆N₂O₄Si
• Molecular Weight: 504.701
• Mol file: 146557-58-6.mol

Synonyms:3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine

Chemical Property of 3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine

There total 12 articles about 3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine 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: 93.0%

allyltributylstanane (24850-33-7) + thiocarbonic acid O-[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-p-tolyl ester (153475-20-8) → 3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine (146557-58-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In toluene; at 80 ℃; for 24h;

DOI:10.1016/S0960-894X(99)00052-9

Reference yield: 89.5%

1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(pentafluorophenoxy)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine (928761-47-1) + allyltributylstanane (24850-33-7) → 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>thymine (121687-74-9) + 3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine (146557-58-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; for 2h; Heating;

DOI:10.1016/j.carres.2006.11.015

Reference yield: 85.0%

allyltributylstanane (24850-33-7) + 1-<5-O-(tert-butyldiphenylsilyl)-3-O-<(phenoxy)thiocarbonyl>-2-deoxy-β-D-erythro-pentofuranosyl>thymine (161085-74-1) → 3-C-allyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine (146557-58-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; for 12h; Reflux;

DOI:10.1055/s-0029-1218357

upstream raw materials:

allyltributylstanane

thiocarbonic acid O-[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-p-tolyl ester

1-<5-O-(tert-butyldiphenylsilyl)-3-O-<(phenoxy)thiocarbonyl>-2-deoxy-β-D-erythro-pentofuranosyl>thymine

1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(1-imidazolyl)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine

Downstream raw materials:

5'-O-(tert-butyldiphenylsilyl)-3'-C-methyleneformyl-3'-deoxythymidine

5'-O-(tert-butyldiphenylsilyl)-3'-C-(1,2-dihydroxy)propyl-3'-deoxythymidine

5'-O-(tert-butyldiphenylsilyl)-3'-C-methylenecarboxylic-3'-deoxythymidine

5'-O-(tert-butyldiphenylsilyl)-3'-C-methylene-N-oximyl-3'-deoxythymidine