(2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester

Base Information

• Chemical Name: (2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester
• CAS No.: 717920-92-8
• Molecular Formula: C₃₁H₃₇O₉PS
• Molecular Weight: 616.669
• Mol file: 717920-92-8.mol

Synonyms:(2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester

Chemical Property of (2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester

There total 5 articles about (2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester 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: 79.0%

3,4-dihydro-2H-pyran (110-87-2) + [(R)-3-(Bis-benzyloxy-phosphoryloxy)-2-hydroxy-propylsulfanyl]-acetic acid benzyl ester (717920-87-1) → (2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester (717920-92-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 30h;

DOI:10.1021/jm031066i

Reference yield:

mercaptoacetic acid benzyl ester (7383-63-3) → (2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester (717920-92-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 55 percent / K₂CO₃ / dimethylformamide / 48 h / 20 °C

2: 67 percent / CuCl₂*2H₂O / propan-2-ol / 3.5 h / 20 °C

3: 21 percent / pyridine / CH₂Cl₂ / 2 h / -78 °C

4: 79 percent / PPTS / CH₂Cl₂ / 30 h / 20 °C

With pyridine; pyridinium p-toluenesulfonate; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm031066i

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (2R)-[3-(bis(benzyloxy)phosphoryloxy)-2-(tetrahydropyran-2-yloxy)propane-1-sulfinyl]acetic acid benzyl ester (717920-92-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / H₂SO₄ / toluene / 2 h / Heating

2: 55 percent / K₂CO₃ / dimethylformamide / 48 h / 20 °C

3: 67 percent / CuCl₂*2H₂O / propan-2-ol / 3.5 h / 20 °C

4: 21 percent / pyridine / CH₂Cl₂ / 2 h / -78 °C

5: 79 percent / PPTS / CH₂Cl₂ / 30 h / 20 °C

With pyridine; sulfuric acid; pyridinium p-toluenesulfonate; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1021/jm031066i

upstream raw materials:

3,4-dihydro-2H-pyran

[(R)-3-(Bis-benzyloxy-phosphoryloxy)-2-hydroxy-propylsulfanyl]-acetic acid benzyl ester

mercaptoacetic acid benzyl ester

benzyl alcohol