(3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene

Base Information

Chemical Name:(3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene
CAS No.:754989-24-7
Molecular Formula:C₁₅H₁₈Cl₃NO₃
Molecular Weight:366.672
Hs Code.:

Synonyms:(3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene

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Chemical Property of (3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene

Chemical Property:

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Technology Process of (3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene

There total 5 articles about (3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene 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:

: 754989-22-5
2,2,2-Trichloro-acetimidic acid (E)-(S)-4-methoxymethoxy-5-phenyl-pent-2-enyl ester

: 754989-24-7
(3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene

: (3S,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene

Guidance literature:: With p-benzoquinone; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1039/b510808j

Reference yield:

: 870290-53-2
ethyl (2E,4S)-4-methoxymethoxy-5-phenylpent-2-enoate

: 754989-24-7
(3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / DIBAL-H / diethyl ether; hexane / -78 - 20 °C

2: DBU / CH₂Cl₂ / 2 h / 20 °C

3: p-benzoquinone / PdCl₂(MeCN)2 / tetrahydrofuran / 24 h / 20 °C

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-benzoquinone; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 3: aza-Claisen rearrangement;
DOI:10.1039/b510808j

Reference yield:

: 20312-36-1
L-3-phenyllactic acid

: 754989-24-7
(3R,4S)-3-(trichloromethylcarbonylamino)-4-(methoxymethoxy)-5-phenylpenta-1-ene

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / aq. HCl / toluene / Heating

2: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 12 h / Heating

3: 70 percent / DIBAL-H / diethyl ether; hexane / -78 - 20 °C

4: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 2.25 h / -78 - 20 °C

5: LiCl; DBU / acetonitrile / 20 °C

6: 83 percent / DIBAL-H / diethyl ether; hexane / -78 - 20 °C

7: DBU / CH₂Cl₂ / 2 h / 20 °C

8: p-benzoquinone / PdCl₂(MeCN)2 / tetrahydrofuran / 24 h / 20 °C

With hydrogenchloride; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; p-benzoquinone; lithium chloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; 4: Swern oxidation / 5: Horner-Wadsworth-Emmons reaction / 8: aza-Claisen rearrangement;
DOI:10.1039/b510808j