(4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one

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Chemical Name:(4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one
CAS No.:264205-87-0
Molecular Formula:C₂₆H₃₁NO₆
Molecular Weight:453.535
Hs Code.:

Synonyms:(4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one

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Chemical Property of (4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one

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Technology Process of (4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one

There total 8 articles about (4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-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: 91.0%

: (4S,5S)-3-Benzoyl-4-[(E)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one

: 264205-87-0
(4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one

Guidance literature:: In water; acetic acid; at 20 ℃;
DOI:10.1039/a909400h

Reference yield:

: 1585-16-6
2-chloromethyl-1,3,5-trimethylbenzene

: 264205-87-0
(4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: Bu₂SnO / toluene

1.2: Bu₄NBr / 80 °C

2.1: DBU / acetonitrile / -30 - -20 °C

3.1: 67 percent / methyl trichloroacetimidate; propylene oxide / acetonitrile / -30 - 0 °C

4.1: PPTS; H₂O / acetone / 20 °C

4.2: 75 percent / H₂O₂ / tetrahydrofuran / 20 °C

5.1: DBU / CH₂Cl₂ / 20 °C

6.1: DMAP; Et₃N / 0 °C

7.1: 91 percent / acetic acid; H₂O / 20 °C

With dmap; water; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; methyloxirane; methyl 2,2,2-trichloroacetimidate; In dichloromethane; water; acetic acid; acetone; toluene; acetonitrile; 1.1: Metallation / 1.2: Substitution / 2.1: Substitution / 3.1: Substitution / 4.1: Hydrolysis / 4.2: Oxidation / 5.1: Cyclization / 6.1: Acylation / 7.1: Ring cleavage;
DOI:10.1039/a909400h

Reference yield:

: 98-88-4
benzoyl chloride

: 264205-87-0
(4S,5S)-3-Benzoyl-4-((E)-(S)-3,4-dihydroxy-but-1-enyl)-5-[2-(2,4,6-trimethyl-benzyloxy)-ethyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: DMAP; Et₃N / 0 °C

2: 91 percent / acetic acid; H₂O / 20 °C

With dmap; triethylamine; In water; acetic acid; 1: Acylation / 2: Ring cleavage;
DOI:10.1039/a909400h