((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester
• CAS No.: 667870-38-4
• Molecular Formula: C₃₉H₅₃NO₇S
• Molecular Weight: 679.918
• Mol file: 667870-38-4.mol

Synonyms:((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester

Chemical Property of ((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester

There total 5 articles about ((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic 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: 94.0%

(dodecylsulfonyl)benzene (78904-63-9) + [(R)-2-Benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid benzyl ester (667870-37-3) → ((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester (667870-38-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1016/j.tetlet.2003.10.142

Reference yield:

1-(benzyloxy)but-3-en-2-ol (93553-66-3) → ((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester (667870-38-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / propionic acid / 2 h / 140 °C

2: Ad-mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

3: 92 percent / Et₃N / CH₂Cl₂

4: 89 percent / NaN₃ / dimethylformamide / 90 °C

5: triphenylphosphine; water / benzene / 8 h

6: Et₃N; DMAP / CH₂Cl₂

7: 94 percent / n-BuLi / tetrahydrofuran / 2 h / -78 °C

With dmap; AD-mix-α; n-butyllithium; sodium azide; methanesulfonamide; water; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/j.tetlet.2003.10.142

Reference yield:

(5S)-5-[(1S)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one (184873-70-9) → ((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester (667870-38-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / Et₃N / CH₂Cl₂

2: 89 percent / NaN₃ / dimethylformamide / 90 °C

3: triphenylphosphine; water / benzene / 8 h

4: Et₃N; DMAP / CH₂Cl₂

5: 94 percent / n-BuLi / tetrahydrofuran / 2 h / -78 °C

With dmap; n-butyllithium; sodium azide; water; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.tetlet.2003.10.142

upstream raw materials:

(dodecylsulfonyl)benzene

[(R)-2-Benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid benzyl ester

1-(benzyloxy)but-3-en-2-ol

(5S)-5-[(1S)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one

Downstream raw materials:

((1R,2S)-1-Benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester