(3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane

Base Information

Chemical Name:(3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane
CAS No.:618893-88-2
Molecular Formula:C₁₅H₂₄NO₅PSi
Molecular Weight:357.419
Hs Code.:

Synonyms:(3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane

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Chemical Property of (3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane

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Technology Process of (3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane

There total 5 articles about (3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane 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: 63.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 618894-24-9
(1S,3S)-(3-amino-4-hydroxy-1-(trimethylsilyl)butyl)phosphonic acid

: 618893-88-2
(3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane

Guidance literature:: With sodium hydrogencarbonate; sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 24h;
DOI:10.1021/jo034707q

Reference yield:

: 57415-84-6
α-trimethylsilylvinylphosphonic acid diethyl ester

: 618893-88-2
(3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 °C

2.1: 88 percent / HCl / tetrahydrofuran / 2 h / 20 °C

3.1: 72 percent / TMSBr / CH₂Cl₂ / 38 h / 0 - 20 °C

4.1: LiBH₄ / tetrahydrofuran / 20 h / 20 °C

5.1: 63 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 24 h / 0 - 20 °C

With hydrogenchloride; lithium borohydride; n-butyllithium; trimethylsilyl bromide; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water;
DOI:10.1021/jo034707q

Reference yield:

: 444789-84-8
(2S,3S)-2-amino-4-(trimethylsilyl)-4-phosphonobutanoic acid

: 618893-88-2
(3S,5S)-5-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(trimethylsilyl)-2-oxo-1,2-oxaphosphorinane

Guidance literature:: Multi-step reaction with 2 steps

1: LiBH₄ / tetrahydrofuran / 20 h / 20 °C

2: 63 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 24 h / 0 - 20 °C

With lithium borohydride; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; water;
DOI:10.1021/jo034707q