5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine

Base Information

• Chemical Name: 5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine
• CAS No.: 927687-33-0
• Molecular Formula: C₃₅H₄₂N₂O₈SSi
• Molecular Weight: 678.879
• Mol file: 927687-33-0.mol

Synonyms:5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine

Chemical Property of 5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine

There total 2 articles about 5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine 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: 77.0%

3'-O-tert-butyldiphenylsilyl-5'-C(R)-(2''-hydroxyethyl)thymidine (927687-31-8) + p-toluenesulfonyl chloride (98-59-9) → 5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine (927687-33-0)

Guidance literature:

With pyridine; In chloroform; at 0 ℃; for 12h;

DOI:10.1002/ejoc.200600593

Reference yield:

3'-O-tert-butyldiphenylsilyl-5'-C(R)-(5''-hydroxy-2''-pentenyl)thymidine (224157-49-7) → 5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine (927687-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-methylmorpholine N-oxide; OsO₄ / acetone; H₂O / 16 h

1.2: NaIO₄ / methanol / 3 h / 0 - 20 °C

1.3: 64 percent / NaBH₄ / ethanol / 12 h / 20 °C

2.1: 77 percent / pyridine / CHCl₃ / 12 h / 0 °C

With pyridine; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In chloroform; water; acetone;

DOI:10.1002/ejoc.200600593

Reference yield: 100.0%

5′-C(R)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine (927687-33-0) + Propargylamine (2450-71-7) → C31H39N3O5Si

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 30 ℃; for 24h;

DOI:10.1039/c9ob01150a

upstream raw materials:

3'-O-tert-butyldiphenylsilyl-5'-C(R)-(2''-hydroxyethyl)thymidine

p-toluenesulfonyl chloride

3'-O-tert-butyldiphenylsilyl-5'-C(R)-(5''-hydroxy-2''-pentenyl)thymidine

Downstream raw materials:

C₄₃H₄₇N₄O₁₄P

C₄₃H₄₇N₄O₁₄P

2-cyanoethyl 3'-O-[5'-O-(4'',4'''-dimethoxytrityl)]thymidinyl-5'-C(R)-2''-tosyloxyethyl-3'-(tert-butyldiphenylsilyl)thymidinyl phosphoric ester

C₅₉H₆₅N₄O₁₄PSi