(2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide

Base Information

Chemical Name:(2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide
CAS No.:221627-43-6
Molecular Formula:C₂₃H₄₁NO₅Si
Molecular Weight:439.668
Hs Code.:

Synonyms:(2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide

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Chemical Property of (2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide

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Technology Process of (2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide

There total 9 articles about (2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide 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: 74.0%

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

: 221627-42-5
(4S)-4-benzyl-(2S,3R,5S)-3-[7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-2-methylheptanoyl]oxazolidin-2-one

: 221627-43-6
(2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide

Guidance literature:: With MeAl; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0040-4039(98)02693-8

Reference yield:

: 106064-33-9
isobutyl 5-(benzyloxy)-3-oxopentanoate

: 221627-43-6
(2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / H₂ / Ru₂Cl₄[(S)-BIMAP]Et₃N / methanol / 60 h / 2585.74 Torr

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

3: 100 percent / DIBAL-H / toluene / 2 h / -78 °C

4: di-n-butylboron triflate; Et₃N / CH₂Cl₂ / -78 - 0 °C

5: 74 percent / Me₃Al / tetrahydrofuran; hexane / 3 h / 0 - 25 °C

With 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; hydrogen; trimethylaluminum; diisobutylaluminium hydride; triethylamine; Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 4: Evans aldol coupling;
DOI:10.1021/jo0503862

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 221627-43-6
(2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran / 0.75 h / 0 °C

1.2: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -25 °C

1.3: 56 percent / tetrahydrofuran; hexane / 1 h / -25 °C

2.1: 99 percent / H₂ / Ru₂Cl₄[(S)-BIMAP]Et₃N / methanol / 60 h / 2585.74 Torr

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

4.1: 100 percent / DIBAL-H / toluene / 2 h / -78 °C

5.1: di-n-butylboron triflate; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: 74 percent / Me₃Al / tetrahydrofuran; hexane / 3 h / 0 - 25 °C

With 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; triethylamine; Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 5.1: Evans aldol coupling;
DOI:10.1021/jo0503862