(S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one

Base Information

• Chemical Name: (S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one
• CAS No.: 1262755-25-8
• Molecular Formula: C₂₇H₃₃NO₅
• Molecular Weight: 451.563
• Mol file: 1262755-25-8.mol

Synonyms:(S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one

Chemical Property of (S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one

There total 5 articles about (S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one 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: 95.0%

diiodomethane (75-11-6) + (S)-4-benzyl-3-[(2S,3R,E)-6-(benzyloxy)-3-hydroxy-2-methylhex-4-enoyl]-5,5-dimethyloxazolidin-2-one (1262755-24-7) → (S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one (1262755-25-8)

Guidance literature:

With diethylzinc; In hexane; dichloromethane; at 0 ℃; for 2h; Darkness; Inert atmosphere;

DOI:10.1021/ol2012023

Reference yield:

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → (S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one (1262755-25-8)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 0.5 h / -55 °C

2: toluene-4-sulfonic acid / dichloromethane / 20 °C

3: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere

4: diethylzinc / hexane; dichloromethane / 2 h / 0 °C / Darkness; Inert atmosphere

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; diethylzinc; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; 3: asymmetric syn-aldol condensation;

DOI:10.1021/ol2012023

Reference yield:

(S)-4-benzyl-5,5-dimethyloxazolidin-2-one (168297-85-6,352438-06-3) → (S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one (1262755-25-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere

3.1: diethylzinc / hexane; dichloromethane / 2 h / 0 °C / Darkness; Inert atmosphere

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; diethylzinc; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: asymmetric syn-aldol condensation;

DOI:10.1021/ol2012023

upstream raw materials:

diiodomethane

(S)-4-benzyl-3-[(2S,3R,E)-6-(benzyloxy)-3-hydroxy-2-methylhex-4-enoyl]-5,5-dimethyloxazolidin-2-one

4-benzyloxycrotonaldehyde

(S)-4-benzyl-5,5-dimethyl-3-propanoyl-1,3-oxazolidin-2-one

Downstream raw materials:

(1S,2S)-2-[(benzyloxy)methyl]cyclopropan-1-carbaldehyde

(S)-4-benzyl-5,5-dimethyl-3-propanoyl-1,3-oxazolidin-2-one

(3S,4R,5R,6R)-6-((benzyloxy)methyl)-4-hydroxy-3,5-dimethyltetrahydro-2H-pyran-2-one

(2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate