2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester
• CAS No.: 552886-69-8
• Molecular Formula: C₂₄H₃₂O₇S
• Molecular Weight: 464.58
• Mol file: 552886-69-8.mol

Synonyms:2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester

There total 3 articles about 2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl 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: 48.0%

p-toluenesulfonyl chloride (98-59-9) + 2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2,3-dihydroxy-propyl ester (552886-84-7) → 2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester (552886-69-8)

Guidance literature:

With triethylamine; at 20 ℃;

DOI:10.3987/com-02-s56

Reference yield:

(2E,4S)-4-<(benzyl)oxy>-2-pentenol (119242-59-0) → 2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester (552886-69-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / MS 4A; TBHP; (+)-diisopropyl tartrate / Ti(OiPr)4 / CH₂Cl₂ / 96 h / -20 °C

2: 64 percent / Ti(OiPr)4 / toluene / Heating

3: 48 percent / Et₃N / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; triethylamine; titanium(IV) isopropylate; In dichloromethane; toluene; 1: Sharpless asymmetric epoxidation;

DOI:10.3987/com-02-s56

Reference yield:

(2S,3S)-3-[(1S)-1-(benzyloxy)ethyl]oxiran-2-ylmethanol (553663-77-7) → 2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl ester (552886-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / Ti(OiPr)4 / toluene / Heating

2: 48 percent / Et₃N / 20 °C

With titanium(IV) isopropylate; triethylamine; In toluene;

DOI:10.3987/com-02-s56

upstream raw materials:

p-toluenesulfonyl chloride

2,2-Dimethyl-propionic acid (1S,2S)-1-((S)-1-benzyloxy-ethyl)-2,3-dihydroxy-propyl ester

(2E,4S)-4-<(benzyl)oxy>-2-pentenol

(2S,3S)-3-[(1S)-1-(benzyloxy)ethyl]oxiran-2-ylmethanol

Downstream raw materials:

2,2-Dimethyl-propionic acid (1R,2S)-1-((S)-1-benzyloxy-ethyl)-2-(tert-butyl-dimethyl-silanyloxy)-3-(toluene-4-sulfonyloxy)-propyl ester

2,2-Dimethyl-propionic acid (1R,2R)-1-((S)-1-benzyloxy-ethyl)-2-(tert-butyl-dimethyl-silanyloxy)-3-iodo-propyl ester