(2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

Base Information

Chemical Name:(2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide
CAS No.:320742-88-9
Molecular Formula:C₃₀H₄₇NO₂Si
Molecular Weight:481.794
Hs Code.:

Synonyms:(2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

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Chemical Property of (2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

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Technology Process of (2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

There total 8 articles about (2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide 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: 83.0%

: 74-88-4
methyl iodide

: 320742-87-8
(2S)-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

: 320742-88-9
(2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

Guidance literature:: (2S)-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

methyl iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃; Further stages.;
DOI:10.1021/ja005526y DOI:10.1016/j.tet.2004.06.014

Reference yield:

: 198124-61-7
(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol

: 320742-88-9
(2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

Guidance literature:: Multi-step reaction with 8 steps

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

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: 63 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

3.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

3.2: 71 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

5.1: 87 percent / NaN₃ / dimethylformamide / 20 °C

6.1: H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

7.1: 826 mg / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 0 - 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.2: 83 percent / tetrahydrofuran; hexane / -78 - 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; sodium azide; diethyl cyanophosphonate; hydrogen; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.014

Reference yield:

: 128329-63-5
(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol

: 320742-88-9
(2S)-N-methyl-N-[(3S,5S)-3,5-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

2.1: 87 percent / NaN₃ / dimethylformamide / 20 °C

3.1: H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

4.1: 826 mg / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 0 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

5.2: 83 percent / tetrahydrofuran; hexane / -78 - 20 °C

With dmap; n-butyllithium; sodium azide; diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.014