2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester

Base Information

Chemical Name:2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester
CAS No.:1412914-87-4
Molecular Formula:C₂₄H₄₅NO₆Si
Molecular Weight:471.71
Hs Code.:

Synonyms:2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester

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Chemical Property of 2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester

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Technology Process of 2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester

There total 8 articles about 2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester 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:

: 2-N-Boc-amino-3-(4-triisopropylsilyloxy-6-triethylsilyloxycyclohex-1-enyl)propionic acid methyl ester

: 1412914-74-9
2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester

: 1412914-87-4
2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester

Guidance literature:: With pyridine hydrogenfluoride; In dichloromethane; at -10 ℃; Overall yield = 93 %; Overall yield = 185 mg; Inert atmosphere;
DOI:10.1021/ja309947n

Reference yield:

: 150-76-5
4-methoxy-phenol

: 1412914-87-4
2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium; ammonia / diethyl ether / 0.75 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

4.1: dmap; 1H-imidazole / dichloromethane / 4 h / 20 °C / Inert atmosphere

5.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / -78 - 40 °C / Inert atmosphere

5.2: 3 h / -40 - 20 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / N,N-dimethyl acetamide / 14 h / 60 °C / Inert atmosphere

7.1: pyridine hydrogenfluoride / dichloromethane / -10 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; ammonia; lithium; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1,1,1,3,3,3-hexamethyl-disilazane; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl acetamide; water; 1.1: |Birch Reduction;
DOI:10.1021/ja309947n

Reference yield:

: Triisopropyl-(4-methoxy-cyclohex-3-enyloxy)-silane

: 1412914-87-4
2-N-Boc-amino-3-(6-hydroxy-4-triisopropylsilyloxycyclohex-1-enyl)propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

2.1: dmap; 1H-imidazole / dichloromethane / 4 h / 20 °C / Inert atmosphere

3.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / -78 - 40 °C / Inert atmosphere

3.2: 3 h / -40 - 20 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / N,N-dimethyl acetamide / 14 h / 60 °C / Inert atmosphere

5.1: pyridine hydrogenfluoride / dichloromethane / -10 °C / Inert atmosphere

With 1H-imidazole; dmap; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1,1,1,3,3,3-hexamethyl-disilazane; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl acetamide; water;
DOI:10.1021/ja309947n