(S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-dienoyl)-oxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-dienoyl)-oxazolidin-2-one
CAS No.:947276-22-4
Molecular Formula:C₁₉H₂₂INO₄
Molecular Weight:455.292
Hs Code.:

Synonyms:(S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-dienoyl)-oxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-dienoyl)-oxazolidin-2-one

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Technology Process of (S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-dienoyl)-oxazolidin-2-one

There total 3 articles about (S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-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:

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

: 799852-92-9
(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienal

: 947276-22-4
(S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-dienoyl)-oxazolidin-2-one

Guidance literature:: (S)-4-benzyl-3-propionyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 0.666667h;

(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienal; In dichloromethane; at -78 ℃; for 0.166667h;

With dihydrogen peroxide; In methanol; phosphate buffer; dichloromethane; at -78 - 20 ℃; Further stages.;
DOI:10.1021/ja0733033

Reference yield:

: 794513-22-7
(2E,4Z)-5-iodo-4-methyl-penta-2,4-dien-1-ol

: 947276-22-4
(S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-dienoyl)-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 0 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

2.2: CH₂Cl₂ / 0.17 h / -78 °C

2.3: 8.12 g / aq. H₂O₂ / methanol; CH₂Cl₂; aq. phosphate buffer / -78 - 20 °C

With di-n-butylboryl trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In dichloromethane; 2.2: Evans syn-aldol addition;
DOI:10.1021/ja0733033

Reference yield:

: 444760-03-6
(2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid methyl ester

: 947276-22-4
(S)-4-benzyl-3-((4E,6Z)-(2S,3R)-3-hydroxy-7-iodo-2,6-dimethyl-hepta-4,6-dienoyl)-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

2.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 0 °C

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

3.2: CH₂Cl₂ / 0.17 h / -78 °C

3.3: 8.12 g / aq. H₂O₂ / methanol; CH₂Cl₂; aq. phosphate buffer / -78 - 20 °C

With di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In dichloromethane; toluene; 3.2: Evans syn-aldol addition;
DOI:10.1021/ja0733033