(S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one

Base Information

Chemical Name:(S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one
CAS No.:160531-16-8
Molecular Formula:C₂₂H₃₃NO₅
Molecular Weight:391.508
Hs Code.:

Synonyms:(S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one

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Chemical Property of (S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one

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Technology Process of (S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one

There total 8 articles about (S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-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: 95.0%

: 77877-19-1,165657-81-8
N-isopropyl oxazolidinone

: 160531-15-7
(S)-3-(benzyloxy)-4-methylpentanal

: 160531-16-8
(S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h;
DOI:10.1021/jo00096a003

Reference yield:

: 16451-50-6
(S)-4-methyl-pentane-1,3-diol

: 160531-16-8
(S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

2: 1.) 60percent NaH, 2.) concd HCl / 1.) DMF, 0 deg C to room temp., 2.5 h, 2.) MeOH, THF, 30 deg C, 4 h

3: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

4: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

With hydrogenchloride; dmap; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

: 160531-37-3
(S)-3-Benzyloxy-4-methyl-pentan-1-ol

: 160531-16-8
(S)-3-((2S,3R,5S)-5-Benzyloxy-3-hydroxy-2,6-dimethyl-heptanoyl)-4-isopropyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

2: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4020(01)81206-0