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

Base Information

Chemical Name:(4S)-4-benzyl-(2S,3R,5S)-3-[7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-2-methylheptanoyl]oxazolidin-2-one
CAS No.:221627-42-5
Molecular Formula:C₃₁H₄₅NO₆Si
Molecular Weight:555.787
Hs Code.:

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

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Chemical Property of (4S)-4-benzyl-(2S,3R,5S)-3-[7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-2-methylheptanoyl]oxazolidin-2-one

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Technology Process of (4S)-4-benzyl-(2S,3R,5S)-3-[7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-2-methylheptanoyl]oxazolidin-2-one

There total 7 articles about (4S)-4-benzyl-(2S,3R,5S)-3-[7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-2-methylheptanoyl]oxazolidin-2-one 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:

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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 131685-53-5,101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: 198754-78-8
(3S)-5-benzyloxy-3-(tert-butyldimethylsilyl)oxypentanal

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

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(98)02693-8

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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