(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide

Base Information

Chemical Name:(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide
CAS No.:947696-76-6
Molecular Formula:C₂₇H₄₁NO₄Si
Molecular Weight:471.712
Hs Code.:

Synonyms:(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide

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Chemical Property of (2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide

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Technology Process of (2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide

There total 4 articles about (2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide 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: 79.0%

: 947696-75-5
(4R,5S)-4-methyl-5-phenyl-3-[(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-2,6-dimethylheptanoyl]-1,3-oxazolidin-2-one

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 947696-76-6
(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In tetrahydrofuran; toluene; at 20 ℃; for 1h;

(4R,5S)-4-methyl-5-phenyl-3-[(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-2,6-dimethylheptanoyl]-1,3-oxazolidin-2-one; In tetrahydrofuran; toluene; at 20 ℃; for 3h; Further stages.;
DOI:10.1002/chem.200700342

Reference yield:

: 371784-89-3
(S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-pentanol

: 947696-76-6
(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / 0 °C

2.1: Et₃N / 0 °C

2.2: 2.5 h / 0 °C

3.1: 79 percent / AlMe₃ / tetrahydrofuran / 3 h / 20 °C

With oxalyl dichloride; trimethylaluminum; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 2.1: Evans asymmetric aldolization;
DOI:10.1016/j.tetlet.2004.08.013

Reference yield:

: 123444-68-8
(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

: 947696-76-6
(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 5.23 g / CH₂Cl₂ / 2.5 h / 0 °C

2.1: Me₃Al / tetrahydrofuran; toluene / 1 h / 20 °C

2.2: 79 percent / tetrahydrofuran; toluene / 3 h / 20 °C

With trimethylaluminum; In tetrahydrofuran; dichloromethane; toluene; 1.1: Evans asymmetric aldolization;
DOI:10.1002/chem.200700342