(+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

Base Information

Chemical Name:(+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate
CAS No.:1091605-49-0
Molecular Formula:C₁₆H₂₁NO₄
Molecular Weight:291.347
Hs Code.:

Synonyms:(+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

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Chemical Property of (+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

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Technology Process of (+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

There total 14 articles about (+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate 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%

: (+)-(S)-benzyl (4-hydroxyhex-5-en-1-yl)carbamate

: 78-94-4,25038-87-3
methyl vinyl ketone

: 1091605-49-0
(+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1016/j.tet.2017.07.041

Reference yield: 60.0%

: C₂₁H₂₉NO₆

: 1091605-49-0
(+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

Guidance literature:: With ammonium cerium (IV) nitrate; In acetonitrile; for 0.416667h; chemoselective reaction; Reflux;
DOI:10.1016/j.tetlet.2018.03.035

Reference yield:

: 87905-98-4
5-<(benzyloxycarbonyl)amino>pentanol

: 1091605-49-0
(+)-(S,E)-benzyl (4-hydroxy-7-oxooct-5-en-1-yl)carbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

2.2: 2.5 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran; acetic acid / 24 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 - 20 °C / Inert atmosphere

5.1: D-Prolin; Nitrosobenzene / dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere

5.2: 20 h / 20 °C / Inert atmosphere

6.1: ammonium cerium (IV) nitrate / acetonitrile / 0.42 h / Reflux

With 1H-imidazole; n-butyllithium; ammonium cerium (IV) nitrate; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; Nitrosobenzene; D-Prolin; In tetrahydrofuran; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; acetonitrile; 5.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tetlet.2018.03.035