(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

Base Information

Chemical Name:(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide
CAS No.:792911-23-0
Molecular Formula:C₃₄H₅₅NO₅Si
Molecular Weight:585.9
Hs Code.:

Synonyms:(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

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Chemical Property of (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

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Technology Process of (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

There total 10 articles about (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide 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: 99.0%

: 132969-64-3
tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane

: 159213-03-3
N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide

: 792911-23-0
(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

Guidance literature:: N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1.41667h;

tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane; In tetrahydrofuran; hexane; at 0 - 20 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tet.2010.01.083

Reference yield:

: 132969-64-3
tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane

: 792911-23-0
(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

Guidance literature:: N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1.66667h;

tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 24h;

Reference yield:

: 792911-22-9
(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

: 792911-23-0
(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: imidazole; ethyldiisopropylamine; iodine / PPh₃ / benzene; diethyl ether; acetonitrile / 0.5 h / 20 °C

2.1: LDA; LiCl / tetrahydrofuran; hexane / -78 - 20 °C

2.2: 87 percent / tetrahydrofuran; hexane / 24 h / 20 °C

With 1H-imidazole; iodine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; acetonitrile; benzene; 2.2: Meyers asymmetric alkylation;
DOI:10.1016/j.tet.2007.05.033