benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

Base Information

Chemical Name:benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate
CAS No.:947595-45-1
Molecular Formula:C₂₀H₂₇NO₄
Molecular Weight:345.439
Hs Code.:

Synonyms:benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

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Chemical Property of benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

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Technology Process of benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

There total 1 articles about benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-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:

: C₁₂H₂₀O₃HNCO

: 33868-53-0
tributylstannyl benzyl ether

: 947595-45-1
benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

: benzyl {(1R,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

Guidance literature:: C₁₂H₂₀O₃HNCO; With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at -10 ℃; for 1.5h;

tributylstannyl benzyl ether; In dichloromethane; at -10 - 20 ℃;

With potassium fluoride; In acetonitrile; at 20 ℃; for 24h; Further stages.;
DOI:10.1021/ol0709735

Reference yield: 92.0%

: 947595-45-1
benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

: 947595-38-2
benzyl {(1S,2E)-1-[(1S,2S)-1,2-dihydroxybut-3-en-1-yl]pent-2-en-1-yl}carbamate

Guidance literature:: With Dowex 50W X₈; In methanol; for 26h; Heating;
DOI:10.1021/ol0709735

Reference yield:

: 947595-45-1
benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

: 947595-46-2
benzyl (3aS,6S,6aS)-6-hydroxy-2,2-dimethyl-6,6a-dihydro-2H-cyclopenta[d][1,3]oxazole-3(3aH)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 92 percent / Dowex 50W x8 / methanol / 26 h / Heating

2.1: 83 percent / (PCy₃)2Cl₂Ru=CHPh / benzene / 15 h / 60 °C

3.1: CSA / acetone / 6 h / 20 °C

3.2: 99 percent / H₂O; silica gel / CH₂Cl₂ / 7 h / 20 °C

With Dowex 50W X₈; camphor-10-sulfonic acid; Grubbs catalyst first generation; In methanol; acetone; benzene;
DOI:10.1021/ol0709735