(1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol

Base Information

• Chemical Name: (1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol
• CAS No.: 866483-39-8
• Molecular Formula: C₁₈H₂₉NO₄
• Molecular Weight: 323.433
• Mol file: 866483-39-8.mol

Synonyms:(1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol

Chemical Property of (1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol

There total 6 articles about (1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol 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:

(R)-1-[(3S,5R)-2-Benzyl-3-(2-hydroxy-ethyl)-3-isobutyl-isoxazolidin-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanol → (1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol (866483-39-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ja0536567

Reference yield:

(1R)-1-[(3S,5R)-3-allyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol (866483-32-1) → (1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol (866483-39-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / iPr₂NEt / dimethylformamide / 0.03 h / microwave irradiation

2: aq. OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran / 5 h / 20 °C

3: aq. NaIO₄ / acetonitrile / 2 h / 20 °C

4: NaBH₄ / methanol / 1 h / cooling

5: 83 mg / TBAF / tetrahydrofuran / 2 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja0536567

Reference yield:

{(3R,5R)-2-Benzyl-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-3-isobutyl-isoxazolidin-3-yl}-acetaldehyde → (1R)-1-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl]ethane-1,2-diol (866483-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 1 h / cooling

2: 83 mg / TBAF / tetrahydrofuran / 2 h / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol;

DOI:10.1021/ja0536567

upstream raw materials:

(1R)-1-[(3S,5R)-3-allyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol

(1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol

benzyl bromide