(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

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Chemical Name:(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol
CAS No.:1132970-05-8
Molecular Formula:C₂₆H₃₇NO₄Si
Molecular Weight:455.67
Hs Code.:

Synonyms:(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

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Chemical Property of (R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

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Technology Process of (R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

There total 11 articles about (R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-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: 92.0%

: 1132969-95-9
(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)-2-(trityloxy)ethanol

: 1132970-05-8
(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

Guidance literature:: With methanol; toluene-4-sulfonic acid; at 20 ℃; for 1.75h; Inert atmosphere;
DOI:10.1002/anie.200804645

Reference yield:

: 1379802-66-0
(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one

: 1132970-05-8
(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

2.2: 0.42 h / 0 °C

3.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

4.1: dichloromethane / -78 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium borohydride; hydroxylamine hydrochloride; toluene-4-sulfonic acid; potassium bromide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1002/chem.201102797

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1132970-05-8
(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 44 h / 20 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

3.2: 0.42 h / 0 °C

4.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

5.1: dichloromethane / -78 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium borohydride; hydroxylamine hydrochloride; toluene-4-sulfonic acid; potassium bromide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.201102797