2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester

Base Information

Chemical Name:2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester
CAS No.:233589-86-1
Molecular Formula:C₂₀H₂₄Cl₃NO₄
Molecular Weight:448.774
Hs Code.:

Synonyms:2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester

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Chemical Property of 2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester

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Technology Process of 2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester

There total 10 articles about 2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester 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: 95.0%

: 545-06-2
trichloroacetonitrile

: 233589-85-0
(E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

: 233589-86-1
2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃;
DOI:10.1016/S0040-4039(99)00911-9

Reference yield:

: 100-39-0
benzyl bromide

: 233589-86-1
2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NaH / dimethylformamide

2: TBAF / tetrahydrofuran

3: imidazole; 2,4,5-triiodoimidazole; (Ph)2P / toluene / Heating

4: 99 percent / Zn / ethanol / Heating

5: methanol

6: 72 percent / LiAlH₄ / tetrahydrofuran / 0 °C

7: 95 percent / DBU / CH₂Cl₂ / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,4,5-triiodoimidazole; tetrabutyl ammonium fluoride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphane; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Hydrolysis / 3: Substitution / 4: Rearrangement / 5: Condensation / 6: Reduction / 7: Esterification;
DOI:10.1016/S0040-4039(99)00911-9

Reference yield:

: 73111-80-5
(2R,3S,4S)-3,4-isopropylidenedioxy-2-benzyloxyhex-5-enal

: 233589-86-1
2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: methanol

2: 72 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3: 95 percent / DBU / CH₂Cl₂ / 0 °C

With lithium aluminium tetrahydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: Reduction / 3: Esterification;
DOI:10.1016/S0040-4039(99)00911-9