tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

Base Information

Chemical Name:tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate
CAS No.:1410805-08-1
Molecular Formula:C₅₂H₇₂N₂O₁₀Si₂
Molecular Weight:941.322
Hs Code.:

tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

Synonyms:tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

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Chemical Property of tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

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Technology Process of tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

There total 14 articles about tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate 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%

: 1410805-06-9
tert-butyl ((R)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-oxoethyl)carbamate

: 1410804-98-6
(R)-3-(3-(benzyloxy)-2-ethynylphenyl)-1-bromo-3-((2-(trimethylsilyl)ethoxy)methoxy)-butan-2-one

: 1410805-07-0
tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

: 1410805-08-1
tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -78 ℃; for 0.5h; Overall yield = 77 %; Overall yield = 1.48 g; Optical yield = 9.091 %de; Inert atmosphere;
DOI:10.1021/ol302691j

Reference yield:

: 1410805-02-5
(S)-tert-butyl 4-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1410805-07-0
tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

: 1410805-08-1
tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

Guidance literature:: Multi-step reaction with 5 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

3.1: acetic acid / methanol / 26 h / 0 °C / Inert atmosphere

4.1: Dess-Martin periodane / 0.58 h / 20 °C / Inert atmosphere

5.1: samarium diiodide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

With samarium diiodide; Dess-Martin periodane; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ol302691j

Reference yield:

: 1410805-03-6
tert-butyl ((S)-1-(3-(benzyloxy)-4-((R)-1-hydroxybut-3-en-1-yl)isoxazol-5-yl)-2-hydroxyethyl)carbamate

: 1410805-07-0
tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

: 1410805-08-1
tert-butyl ((1S,5R)-5-(3-(benzyloxy)-2-ethynylphenyl)-1-(3-(benzyloxy)-4-((R)-1-((triethylsilyl)oxy)but-3-en-1-yl)isoxazol-5-yl)-2-hydroxy-4-oxo-5-((2-(trimethylsilyl)ethoxy)methoxy)hexyl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

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

2: acetic acid / methanol / 26 h / 0 °C / Inert atmosphere

3: Dess-Martin periodane / 0.58 h / 20 °C / Inert atmosphere

4: samarium diiodide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

With samarium diiodide; Dess-Martin periodane; acetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ol302691j