(E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl ester
CAS No.:544455-43-8
Molecular Formula:C₂₈H₃₅NO₇
Molecular Weight:497.588
Hs Code.:

Synonyms:(E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl ester

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Chemical Property of (E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl ester

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Technology Process of (E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl ester

There total 9 articles about (E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl 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: 94.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 544455-42-7
N-allyl-N-[2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-3-oxo-propyl]-acetamide

: 544455-43-8
(E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; In tetrahydrofuran; at 25 ℃; for 2h;
DOI:10.1016/S0040-4039(03)00218-1

Reference yield:

: 150-76-5
4-methoxy-phenol

: 544455-43-8
(E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 70 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; LiOH / 2-methyl-propan-2-ol; H₂O / 8 h / 4 °C

2: 80 percent / NaH / dimethylformamide / 8 h / 0 °C

3: 100 percent / LiBH₄ / diethyl ether / 0.25 h

4: 100 percent / TEA; DMAP / CH₂Cl₂ / 4 h / 25 °C

5: 95 percent / KH; 18-crown-ether / tetrahydrofuran / 5 h / 25 °C

6: 100 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C

7: 90 percent / periodinane / CH₂Cl₂ / 1 h / 25 °C

8: 94 percent / LiBr; DBU / tetrahydrofuran / 2 h / 25 °C

With dmap; lithium hydroxide; potassium osmate(VI); lithium borohydride; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Sharpless asymmetric aminohydroxylation / 8: Dess-Martin oxidation / 9: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/S0040-4039(03)00218-1

Reference yield:

: 544455-38-1
ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate

: 544455-43-8
(E)-(4R,5R)-5-(Acetyl-allyl-amino)-4-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxy)-hex-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; LiOH / 2-methyl-propan-2-ol; H₂O / 8 h / 4 °C

2: 80 percent / NaH / dimethylformamide / 8 h / 0 °C

3: 100 percent / LiBH₄ / diethyl ether / 0.25 h

4: 100 percent / TEA; DMAP / CH₂Cl₂ / 4 h / 25 °C

5: 95 percent / KH; 18-crown-ether / tetrahydrofuran / 5 h / 25 °C

6: 100 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C

7: 90 percent / periodinane / CH₂Cl₂ / 1 h / 25 °C

8: 94 percent / LiBr; DBU / tetrahydrofuran / 2 h / 25 °C

With dmap; lithium hydroxide; potassium osmate(VI); lithium borohydride; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Sharpless asymmetric aminohydroxylation / 7: Dess-Martin oxidation / 8: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/S0040-4039(03)00218-1