(2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

Base Information

Chemical Name:(2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide
CAS No.:851955-72-1
Molecular Formula:C₂₄H₄₃NO₄Si
Molecular Weight:437.695
Hs Code.:

Synonyms:(2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

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Chemical Property of (2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

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Technology Process of (2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

There total 5 articles about (2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide 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:

: 851955-69-6
5-(benzyloxy)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpentanamide

: 851955-72-1
(2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / LiCl; iPr₂NH; BuLi / tetrahydrofuran; hexane / 0.75 h / 0 °C

2.1: 75 percent / iPr₂NH; BuLi; BH₃*NH₃ / hexane; tetrahydrofuran / 16 h / 20 °C

3.1: 84 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -78 - -30 °C

4.1: Bu₂B-OTf; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4.2: 8 g / Me₃Al / tetrahydrofuran; hexane / 16 h / -5 - 20 °C

5.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; borane-ammonia complex; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; 3.1: Swern oxidation;
DOI:10.1016/j.bioorg.2004.11.002

Reference yield:

: 851955-70-9
(2S)-5-(benzyloxy)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethylpentanamide

: 851955-72-1
(2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / iPr₂NH; BuLi; BH₃*NH₃ / hexane; tetrahydrofuran / 16 h / 20 °C

2.1: 84 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -78 - -30 °C

3.1: Bu₂B-OTf; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

3.2: 8 g / Me₃Al / tetrahydrofuran; hexane / 16 h / -5 - 20 °C

4.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; borane-ammonia complex; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation;
DOI:10.1016/j.bioorg.2004.11.002

Reference yield:

: 64740-39-2
5-benzyloxypentanoic acid

: 851955-72-1
(2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 6 steps

1.1: Et₃N; pivaloyl chloride / acetonitrile; tetrahydrofuran / 0.5 h / 0 °C

1.2: 87 percent / Et₃N / acetonitrile; tetrahydrofuran / 3 h / 0 - 20 °C

2.1: 94 percent / LiCl; iPr₂NH; BuLi / tetrahydrofuran; hexane / 0.75 h / 0 °C

3.1: 75 percent / iPr₂NH; BuLi; BH₃*NH₃ / hexane; tetrahydrofuran / 16 h / 20 °C

4.1: 84 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -78 - -30 °C

5.1: Bu₂B-OTf; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

5.2: 8 g / Me₃Al / tetrahydrofuran; hexane / 16 h / -5 - 20 °C

6.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; borane-ammonia complex; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pivaloyl chloride; dimethyl sulfoxide; triethylamine; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 4.1: Swern oxidation;
DOI:10.1016/j.bioorg.2004.11.002