Methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-Methylbenzenesulfonyl)-D-erythro-pentofuranoside

Base Information

• Chemical Name: Methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-Methylbenzenesulfonyl)-D-erythro-pentofuranoside
• CAS No.: 152039-44-6
• Molecular Formula: C29H36O6SSi
• Molecular Weight: 540.753
• Mol file: 152039-44-6.mol

Synonyms:Methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-Methylbenzenesulfonyl)-D-erythro-pentofuranoside

Chemical Property of Methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-Methylbenzenesulfonyl)-D-erythro-pentofuranoside

Chemical Property:

• PSA: 79.44000
• LogP: 5.48770

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-Methylbenzenesulfonyl)-D-erythro-pentofuranoside

There total 1 articles about Methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-Methylbenzenesulfonyl)-D-erythro-pentofuranoside 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:

methyl-2-deoxyribopyranoside (863396-35-4) + p-toluenesulfonyl chloride (98-59-9) + tert-butylchlorodiphenylsilane (58479-61-1) → methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methylbenzenesulfonyl)-D-erythro-pentofuranoside (152039-44-6)

Guidance literature:

With dmap; Yield given. Multistep reaction; 1.) 2 h, r.t., pyridine; 2.) 12 h, r.t., dioxane;

DOI:10.1055/s-1995-4070

Reference yield: 54.0%

methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methylbenzenesulfonyl)-D-erythro-pentofuranoside (152039-44-6) + 2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine (33282-64-3) → 5-bromo-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-α-D-erythro-pentofuranosyl)uracil + 5-bromo-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)uracil (172473-15-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -30 ℃; for 5h; Yield given;

DOI:10.1055/s-1995-4070

Reference yield: 54.0%

methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methylbenzenesulfonyl)-D-erythro-pentofuranoside (152039-44-6) + 2,4-bis-trimethylsilyloxy-5-ethylpyrimidine (31167-05-2) → 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-α-D-erythro-pentofuranosyl)-5-ethyluracil + 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-ethyluracil (172473-13-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -30 ℃; for 5h; Yield given;

DOI:10.1055/s-1995-4070

upstream raw materials:

methyl-2-deoxyribopyranoside

p-toluenesulfonyl chloride

tert-butylchlorodiphenylsilane

Downstream raw materials:

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-iodouracil

5-bromo-1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)uracil

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)uracil