6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester

Base Information

• Chemical Name: 6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester
• CAS No.: 179462-40-9
• Molecular Formula: C₂₆H₄₅NO₅Si
• Molecular Weight: 479.733
• Mol file: 179462-40-9.mol

Synonyms:6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester

Chemical Property of 6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester

There total 1 articles about 6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl 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: 35.0%

(3S,4R)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-ol + methyl (Z)-6-benzyliminoheptanoate N-oxide → 6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester (179462-40-9) + 6-{(3S,5R)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester (179462-39-6) + 6-{(3R,5R)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester (179123-17-2)

Guidance literature:

In toluene; for 60h; Product distribution; Heating; other solvent, reaction time, temperature, effect of addition of MeMgBr;

DOI:10.1016/S0040-4020(98)01012-6

Reference yield: 66.0%

2-Methoxyethoxymethyl chloride (3970-21-6) + 6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester (179462-40-9) → 6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester (220023-63-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 25h; Heating;

DOI:10.1016/S0040-4020(98)01012-6

Reference yield:

6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester (179462-40-9) → 6-{(3R,5S)-2-Benzyl-5-[(1R,2R)-2-hydroxy-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester (220023-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / DIPEA / CH₂Cl₂ / 25 h / Heating

2: 82 percent / TBAF / tetrahydrofuran / 9 h / Heating

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(98)01012-6

Downstream raw materials:

6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester

6-{(3R,5S)-2-Benzyl-5-[(1R,2R)-2-hydroxy-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester

6-{(3R,5S)-2-Benzyl-5-[(1S,2R)-2-methanesulfonyloxy-1-(2-methoxy-ethoxymethoxy)-propyl]-isoxazolidin-3-yl}-hexanoic acid methyl ester