(S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one
CAS No.:1610887-89-2
Molecular Formula:C₃₀H₃₇NO₆
Molecular Weight:507.627
Hs Code.:

Synonyms:(S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one

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Technology Process of (S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one

There total 3 articles about (S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]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:

: (S)-4-benzyl-3-{(1E,3E)-1[(tert-butyldimethylsilyl)oxy]-2-methylpenta-1,3-diene-1-yl}oxazolidin-2-one

: 1610887-88-1
(3R,4R)-3-(benzyloxy)-4-methoxyhex-5-enal

: (S)-4-benzyl-3-[(7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one

: 1610887-89-2
(S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one

Guidance literature:: (3R,4R)-3-(benzyloxy)-4-methoxyhex-5-enal; With titanium(IV) trichloride isopropoxide; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

(S)-4-benzyl-3-{(1E,3E)-1[(tert-butyldimethylsilyl)oxy]-2-methylpenta-1,3-diene-1-yl}oxazolidin-2-one; In dichloromethane; at -50 ℃; for 48h; Inert atmosphere;

With sodium hydrogencarbonate; rochelle salt; In dichloromethane; at 20 ℃; for 24h; Overall yield = 42 %; Overall yield = 0.045 g; Inert atmosphere;
DOI:10.1021/ol5011278

Reference yield:

: 1610887-83-6
(3R,4R)-4-methoxy-1-(4-methoxybenzyloxy)hex-5-ene-3-ol

: 1610887-89-2
(S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

3.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.25 h / -78 - -45 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: titanium(IV) trichloride isopropoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: 48 h / -50 °C / Inert atmosphere

4.3: 24 h / 20 °C / Inert atmosphere

With oxalyl dichloride; titanium(IV) trichloride isopropoxide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1021/ol5011278

Reference yield:

: 1610887-87-0
(3R,4R)-3-(benzyloxy)-4-methoxyhex-5-ene-1-ol

: 1610887-89-2
(S)-4-benzyl-3-[(4S,5S,7R,8R,E)-7-(benzyloxy)-5-hydroxy-8-methoxy-2,4-dimethyldeca-2,9-dienoyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.25 h / -78 - -45 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: titanium(IV) trichloride isopropoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 48 h / -50 °C / Inert atmosphere

2.3: 24 h / 20 °C / Inert atmosphere

With oxalyl dichloride; titanium(IV) trichloride isopropoxide; dimethyl sulfoxide; In dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1021/ol5011278