(4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

Base Information

Chemical Name:(4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone
CAS No.:183960-57-8
Molecular Formula:C₂₉H₃₄BrNO₅
Molecular Weight:556.497
Hs Code.:

Synonyms:(4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

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Chemical Property of (4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

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Technology Process of (4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

There total 6 articles about (4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone 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: 79.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 183960-80-7
(4R)-4-benzyl-3-((2R,3S,4R,5S,6S)-8-bromo-3,5-dihydroxy-2,4,6-trimethyl-1-oxo-8-nonenyl)-2-oxazolidinone

: 183960-57-8
(4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

Guidance literature:: With camphor-10-sulfonic acid; for 10h; under 10 Torr; Ambient temperature;
DOI:10.1021/ja9806128

Reference yield:

: 101712-01-0,141423-22-5,141423-21-4
(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione

: 183960-57-8
(4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) TiCl₄, Ti(i-OPr)4, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 45 min

2: 89 percent / Zn(BH₄)2 / CH₂Cl₂; diethyl ether / a) -78 deg C, 15 min, b) -50 deg C, 1.5 h

3: 79 percent / CSA / 10 h / 10 Torr / Ambient temperature

With titanium(IV) isopropylate; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; titanium tetrachloride; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1021/ja9806128

Reference yield:

: 113453-47-7
(S)-4-bromo-2-methylpent-4-enal

: 183960-57-8
(4R)-4-benzyl-3-{(2R)-2-[(2S,4S,5S,6S)-6-((1S)-3-bromo-1-methyl-3-butenyl)-5-methyl-2-phenyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) TiCl₄, Ti(i-OPr)4, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 45 min

2: 89 percent / Zn(BH₄)2 / CH₂Cl₂; diethyl ether / a) -78 deg C, 15 min, b) -50 deg C, 1.5 h

3: 79 percent / CSA / 10 h / 10 Torr / Ambient temperature

With titanium(IV) isopropylate; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; titanium tetrachloride; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1021/ja9806128