N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide

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Chemical Name:N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide
CAS No.:233589-87-2
Molecular Formula:C₂₀H₂₄Cl₃NO₄
Molecular Weight:448.774
Hs Code.:

Synonyms:N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide

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Chemical Property of N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide

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Technology Process of N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide

There total 9 articles about N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-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: 73.0%

: 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

: 233589-87-2
N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide

Guidance literature:: dichloro bis(acetonitrile) palladium(II); In toluene; at 20 ℃; for 12h;
DOI:10.1016/S0040-4039(99)00911-9

Reference yield:

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

: 233589-87-2
N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1: methanol

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

3: 95 percent / DBU / CH₂Cl₂ / 0 °C

4: 73 percent / PdCl₂(MeCN)2 / toluene / 12 h / 20 °C

With lithium aluminium tetrahydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Condensation / 2: Reduction / 3: Esterification / 4: Rearrangement;
DOI:10.1016/S0040-4039(99)00911-9

Reference yield:

: 100-39-0
benzyl bromide

: 233589-87-2
N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide

Guidance literature:: Multi-step reaction with 8 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

8: 73 percent / PdCl₂(MeCN)2 / toluene / 12 h / 20 °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; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Hydrolysis / 3: Substitution / 4: Rearrangement / 5: Condensation / 6: Reduction / 7: Esterification / 8: Rearrangement;
DOI:10.1016/S0040-4039(99)00911-9