(8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate

Base Information

• Chemical Name: (8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate
• CAS No.: 1579224-91-1
• Molecular Formula: C₃₅H₅₉NO₈S
• Molecular Weight: 653.921
• Mol file: 1579224-91-1.mol

Synonyms:(8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate

Chemical Property of (8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate

There total 8 articles about (8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate 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: 88.0%

(S)-4-benzyl-3-((2S,3R,5R)-2-decyl-3-hydroxy-5-(methoxymethoxy)dodecanoyl)oxazolidin-2-one (1579224-86-4) + methanesulfonyl chloride (124-63-0) → (8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate (1579224-91-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.02.010

Reference yield:

(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone (198649-20-6) → (8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate (1579224-91-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

1.2: Evans Aldol Reaction / 0.67 h / 0 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With titanium tetrachloride; triethylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2014.02.010

Reference yield:

Octanal (124-13-0) → (8R,10R,11S)-11-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-8-(methoxymethoxy)henicosan-10-ylmethanesulfonate (1579224-91-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: titanium tetrachloride; silver(l) oxide; (R)-1,1'-Bi-2-naphthol; titanium(IV) isopropylate / dichloromethane / 12 h / -15 - 0 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C

2.2: 3 h / 0 - 20 °C

3.1: ozone / dichloromethane / 1 h / -78 °C

4.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

4.2: Evans Aldol Reaction / 0.67 h / 0 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; In dichloromethane;

DOI:10.1016/j.tetlet.2014.02.010

upstream raw materials:

(S)-4-benzyl-3-((2S,3R,5R)-2-decyl-3-hydroxy-5-(methoxymethoxy)dodecanoyl)oxazolidin-2-one

methanesulfonyl chloride

(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

Octanal