(S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 1410805-02-5
• Molecular Formula: C₂₄H₃₂N₂O₆
• Molecular Weight: 444.528
• Mol file: 1410805-02-5.mol

Synonyms:(S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property of (S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

There total 1 articles about (S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate 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:

Leighton reagent A + (S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate (1410805-01-4) → (S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate (1410805-02-5) + (S)-tert-butyl 4-(3-(benzyloxy)-4-((S)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate (1410805-65-0)

Guidance literature:

In toluene; at -10 - 20 ℃; for 84h; Overall yield = 78 %; Overall yield = 10.58 g; Inert atmosphere;

DOI:10.1021/ol302691j

Reference yield: 99.0%

(S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate (1410805-02-5) → tert-butyl ((S)-1-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2-hydroxyethyl)carbamate (1410805-03-6)

Guidance literature:

(S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate; With trifluoroacetic acid; In methanol; at 0 ℃; for 0.5h; Inert atmosphere;

With di-tert-butyl dicarbonate; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol302691j

Reference yield:

(S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate (1410805-02-5) → tert-butyl ((S)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-((triethylsilyl)oxy)ethyl)carbamate (1410805-04-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / methanol / 0.5 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

2.1: N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

With trifluoroacetic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol302691j

upstream raw materials:

(S)-tert-butyl 4-(3-(benzyloxy)-4-formylisoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

Downstream raw materials:

tert-butyl ((S)-1-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2-hydroxyethyl)carbamate

tert-butyl ((S)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-((triethylsilyl)oxy)ethyl)carbamate

tert-butyl ((S)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxyethyl)carbamate

tert-butyl ((R)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-oxoethyl)carbamate