(E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine

Base Information

• Chemical Name: (E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine
• CAS No.: 134939-01-8
• Molecular Formula: C₂₅H₂₅BrN₂O₄S
• Molecular Weight: 529.454
• Mol file: 134939-01-8.mol

Synonyms:

Chemical Property of (E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine

There total 2 articles about (E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine 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:

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside (134938-97-9) → (E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine (134939-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / CCl₄ / 25 °C

2: 2.) methanol / 1.) a) CCl₄, RT, 1 h, b) 90-100 deg C, 1 h, 2.) H₂O, reflux, 1 h

With methanol; bromine; In tetrachloromethane;

DOI:10.1021/jm00113a016

Reference yield:

2,4-bis-O-(trimethylsilyl)-(E)-5-(2-bromovinyl)uracil (73446-72-7) + (2R,3S)-3-Benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-thiophene (134967-13-8) → 5-((E)-2-Bromo-vinyl)-1-((R)-5-methylene-2,5-dihydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione (134939-02-9) + (E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine (134939-01-8) + α-(E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine (134939-03-0)

Guidance literature:

With methanol; Yield given. Multistep reaction. Yields of byproduct given; 1.) a) CCl₄, RT, 1 h, b) 90-100 deg C, 1 h, 2.) H₂O, reflux, 1 h;

DOI:10.1021/jm00113a016

Reference yield:

(E)-5-(2-bromovinyl)-3',5'-di-O-benzyl-2'-deoxy-4'-thiothymidine (134939-01-8) → (E)-5-(2-bromovinyl)-2'-deoxy-4'-thiouridine (134699-93-7)

Guidance literature:

With methanol; boron trichloride; Multistep reaction; 1.) CH₂Cl₂, -78 deg C, 5 h, 2.) CH₂Cl₂, from -78 deg C to RT, 1 h;

DOI:10.1021/jm00113a016

upstream raw materials:

2,4-bis-O-(trimethylsilyl)-(E)-5-(2-bromovinyl)uracil

(2R,3S)-3-Benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-thiophene

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside

Downstream raw materials:

(E)-5-(2-bromovinyl)-2'-deoxy-4'-thiouridine

Refernces