2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide

Base Information

Chemical Name:2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide
CAS No.:143842-79-9
Molecular Formula:C₂₂H₃₁NO₃
Molecular Weight:357.493
Hs Code.:

Synonyms:2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide

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Chemical Property of 2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide

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Technology Process of 2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide

There total 8 articles about 2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide 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: 84.0%

: 143842-78-8
<1S-<1α,3(S^*),6α>>-3-<4-hydroxy-2-(phenylmethoxy)butyl>-N,N,6-trimethyl-2-cyclohexene-1-acetamide

: 143842-79-9
2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -30 ℃; for 0.05h;
DOI:10.1021/jo00052a029

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 143842-79-9
2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: 79 percent / CF₃SO₃H / CH₂Cl₂; cyclohexane / Ambient temperature

2: 1) aq. KOH, 2) I₂, KI, 3) 1,4-diazabicyclo<2.2.2>octane / 1) MeOH, r.t., 2) H₂O, hexane, EtOAc, r.t., 1 h, 3) DMSO, 132-140 deg C, 15 min

3: diisobutylaluminium hydride / CH₂Cl₂ / 0 °C

4: 1) KOtBu / 1) THF, 1 h, r.t., 2) THF, r.t., 1 h

5: 92 percent / 48 h / 130 °C

6: 1) disiamylborane, BH₃*SMe₂, 2) 30percent H₂O₂ / 1) THF, r.t., 30 min, 2) MeOH

7: 84 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.05 h / -30 °C

With 1,4-diaza-bicyclo[2.2.2]octane; potassium hydroxide; oxalyl dichloride; trifluorormethanesulfonic acid; dimethylsulfide borane complex; potassium tert-butylate; dihydrogen peroxide; iodine; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; dimethyl sulfoxide; potassium iodide; In dichloromethane; cyclohexane;
DOI:10.1021/jo00052a029

Reference yield:

: 143842-76-6
(1S,4S)-1-((R)-2-Benzyloxy-but-3-enyl)-4-methyl-cyclohex-2-enol

: 143842-79-9
2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / 48 h / 130 °C

2: 1) disiamylborane, BH₃*SMe₂, 2) 30percent H₂O₂ / 1) THF, r.t., 30 min, 2) MeOH

3: 84 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.05 h / -30 °C

With oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; dimethyl sulfoxide; In dichloromethane;
DOI:10.1021/jo00052a029