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

Base Information

• Chemical Name: (1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol
• CAS No.: 866483-36-5
• Molecular Formula: C₂₅H₄₃NO₃Si
• Molecular Weight: 433.707
• Mol file: 866483-36-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol 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: 77.0%

(1R)-1-[(3S,5R)-3-allyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol (866483-32-1) + benzyl bromide (100-39-0) → (1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol (866483-36-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.0333333h; microwave irradiation;

DOI:10.1021/ja0536567

Reference yield:

(1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol (866483-36-5) → (R)-1-[(3S,5R)-2-Benzyl-3-(2-hydroxy-ethyl)-3-isobutyl-isoxazolidin-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanol

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: NaBH₄ / methanol / 1 h / cooling

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; methanol; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja0536567

Reference yield:

(1R)-1-[(3S,5R)-3-allyl-2-benzyl-3-isobutylisoxazolidin-5-yl]-2-(tert-butyldimethylsilanyloxy)ethanol (866483-36-5) → 4-[(3S,5R)-2-benzyl-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-ylmethylenehydrazinocarbonyl]-2-{4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoylamino}-(S)-butyric acid

Guidance literature:

Multi-step reaction with 6 steps

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

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

3: NaBH₄ / methanol / 1 h / cooling

4: 83 mg / TBAF / tetrahydrofuran / 2 h / 20 °C

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

6: tetrahydrofuran; dimethylformamide / 24 h / 20 °C

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

DOI:10.1021/ja0536567

upstream raw materials:

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

benzyl bromide

Downstream raw materials:

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