(2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

Base Information

Chemical Name:(2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide
CAS No.:866923-94-6
Molecular Formula:C₃₄H₄₇NO₃Si
Molecular Weight:545.838
Hs Code.:

Synonyms:(2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

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Chemical Property of (2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

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Technology Process of (2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

There total 4 articles about (2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide 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: 93.0%

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

: 275804-95-0
(3R)-4-iodo-3-methyl-1-butyl tert-butyldiphenylsilyl ether

: 866923-94-6
(2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

Guidance literature:: N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 23 ℃; for 1.33333h; Inert atmosphere;

(3R)-4-iodo-3-methyl-1-butyl tert-butyldiphenylsilyl ether; In tetrahydrofuran; hexane; at 0 - 23 ℃; for 18h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/anie.201102037

Reference yield:

: 913183-55-8
(R)-4-(tert-butyldiphenylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-n,2-dimethylbutanamide

: 866923-94-6
(2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: borane-ammonia complex; n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / 0 - 23 °C / Inert atmosphere

1.2: 0.5 h / 0 °C / Inert atmosphere

2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2 h / 23 °C / Inert atmosphere

3.1: n-butyllithium; diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C / Inert atmosphere

3.2: 18 h / 0 - 23 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; borane-ammonia complex; iodine; diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/anie.201102037

Reference yield:

: 126822-71-7
1-iodo-2-<(tert-butyldiphenylsilyl)oxy>ethane

: 866923-94-6
(2R,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium; diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C / Inert atmosphere

1.2: 18 h / 0 - 20 °C / Inert atmosphere

2.1: borane-ammonia complex; n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / 0 - 23 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2 h / 23 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C / Inert atmosphere

4.2: 18 h / 0 - 23 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; borane-ammonia complex; iodine; diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/anie.201102037