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

Base Information

• Chemical Name: (2R,3S)-3-Benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-thiophene
• CAS No.: 134967-13-8
• Molecular Formula: C₁₉H₂₁BrO₂S
• Molecular Weight: 393.345
• Mol file: 134967-13-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2R,3S)-3-Benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-thiophene 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) → (2R,3S)-3-Benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-thiophene (134967-13-8)

Guidance literature:

With bromine; In tetrachloromethane; at 25 ℃;

DOI:10.1021/jm00113a016

Reference yield:

(2R,3S)-3-Benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-thiophene (134967-13-8) → (E)-5-(2-bromovinyl)-2'-deoxy-4'-thiouridine (134699-93-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 1.) BCl₃, 2.) methanol / 1.) CH₂Cl₂, -78 deg C, 5 h, 2.) CH₂Cl₂, from -78 deg C to RT, 1 h

With methanol; boron trichloride;

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

upstream raw materials:

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

Downstream raw materials:

5-((E)-2-Bromo-vinyl)-1-((R)-5-methylene-2,5-dihydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione

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

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

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