(E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl ester

Base Information

Chemical Name:(E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl ester
CAS No.:861903-04-0
Molecular Formula:C₂₁H₃₀O₇
Molecular Weight:394.465
Hs Code.:

Synonyms:(E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl ester

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Chemical Property of (E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl ester

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Technology Process of (E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl ester

There total 6 articles about (E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl 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: 76.0%

: 861902-95-6
(E,4R,5S)-4-((2-methoxyethoxy)methoxy)-5-(4-methoxybenzyloxy)hex-2-enoic acid

: 106-95-6
allyl bromide

: 861903-04-0
(E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl ester

Guidance literature:: With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1021/ol0508429

Reference yield:

: 861902-93-4
(S)-N-methoxy-2-((4-methoxybenzyl)oxy)-N-methylpropanamide

: 861903-04-0
(E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: t-BuLi / diethyl ether; pentane / 5 h / -40 °C

1.2: 90 percent / pentane; diethyl ether / 12 h / 20 °C

2.1: 91 percent / LiEt₃BH / tetrahydrofuran; CH₂Cl₂ / 0.17 h / -78 °C

3.1: iPr₂NEt / CH₂Cl₂ / 41 h / 20 °C

4.1: 76 mg / HCl / H₂O; tetrahydrofuran / 0.17 h / 20 °C

5.1: 76 percent / KHCO₃ / dimethylformamide / 12 h / 20 °C

With hydrogenchloride; tert.-butyl lithium; lithium triethylborohydride; potassium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol0508429

Reference yield:

: 861902-90-1
(E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

: 861903-04-0
(E)-(4R,5S)-5-(4-Methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-hex-2-enoic acid allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: iPr₂NEt / CH₂Cl₂ / 41 h / 20 °C

2: 76 mg / HCl / H₂O; tetrahydrofuran / 0.17 h / 20 °C

3: 76 percent / KHCO₃ / dimethylformamide / 12 h / 20 °C

With hydrogenchloride; potassium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0508429