methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate

Base Information

Chemical Name:methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate
CAS No.:1630067-65-0
Molecular Formula:C₂₀H₂₉NO₄
Molecular Weight:347.455
Hs Code.:

Synonyms:methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate

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Chemical Property of methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate

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Technology Process of methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate

There total 5 articles about methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-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: 91.7%

: 1630067-64-9
methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-(methoxymethoxy)-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate

: 1630067-65-0
methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate

Guidance literature:: With hydrogenchloride; In methanol; at 0 - 20 ℃; for 9.16667h; Inert atmosphere;
DOI:10.1002/ejoc.201402452

Reference yield:

: 1630067-58-1
(R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-ol

: 1630067-65-0
methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 5.17 h / 0 °C / Inert atmosphere

2.1: chloro-trimethyl-silane; lithium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 2.83 h / -78 - -20 °C / Inert atmosphere

3.1: di-tert-butyl dicarbonate; pyridine / ethyl acetate / 3 h / 20 °C / Inert atmosphere

3.2: 2 h / Inert atmosphere

4.1: aluminum (III) chloride; lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 12 h / 0 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

6.1: hydrogenchloride / methanol / 9.17 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; aluminum (III) chloride; lithium aluminium tetrahydride; chloro-trimethyl-silane; di-tert-butyl dicarbonate; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.201402452

Reference yield:

: 1630067-59-2
(R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-yl 3-methylbut-3-enoate

: 1630067-65-0
methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(prop-1-en-2-yl)hex-4-en-1-yl}carbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: chloro-trimethyl-silane; lithium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 2.83 h / -78 - -20 °C / Inert atmosphere

2.1: di-tert-butyl dicarbonate; pyridine / ethyl acetate / 3 h / 20 °C / Inert atmosphere

2.2: 2 h / Inert atmosphere

3.1: aluminum (III) chloride; lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 12 h / 0 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.1: hydrogenchloride / methanol / 9.17 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; aluminum (III) chloride; lithium aluminium tetrahydride; chloro-trimethyl-silane; di-tert-butyl dicarbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.201402452