1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol

Base Information

• Chemical Name: 1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol
• CAS No.: 404870-10-6
• Molecular Formula: C₂₀H₂₀F₂O₂S
• Molecular Weight: 362.44
• Mol file: 404870-10-6.mol

Synonyms:1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol

Chemical Property of 1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol

There total 1 articles about 1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol 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: 47.0%

dibromodifluoromethane (75-61-6) + (4S,5R)-4-Benzyloxy-5-benzyloxymethyl-dihydro-thiophen-3-one → 1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol (404870-10-6)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; zinc; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/ol017112v

Reference yield:

1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol (404870-10-6) → (2R,3S)-3-Benzyloxy-2-benzyloxymethyl-4-difluoromethylene-tetrahydro-thiophene 1-oxide

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 0.666667h;

DOI:10.1021/ol017112v

Reference yield:

1,4-anhydro-2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol (404870-10-6) → N4-benzoyl-1-(2-deoxy-3,5-dibenzoyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine (404870-19-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / BBr₃ / CH₂Cl₂ / 3 h / -78 °C

2.1: 95 percent / pyridine / 1 h / 20 °C

3.1: mCPBA / CH₂Cl₂ / 1 h / -78 °C

3.2: 36 percent / TMSOTf / 1,2-dichloro-ethane / 1 h / 0 - 50 °C

With pyridine; boron tribromide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ol017112v

upstream raw materials:

dibromodifluoromethane

Downstream raw materials:

1,4-anhydro-2-deoxy-3,5-dibenzoyl-2-C-difluoromethylene-4-thio-D-erythro-pentitol

N⁴-acetyl-1-(2-deoxy-3,5-dibenzyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine

N⁴-benzoyl-1-(2-deoxy-3,5-di-t-butyldimethylsilyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine

N⁴-benzoyl-1-(2-deoxy-3,5-dibenzoyl-2-C-difluoromethylene-4-thio-β-D-erythro-pentofuranosyl)cytosine