(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

Base Information

Chemical Name:(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate
CAS No.:1335286-87-7
Molecular Formula:C₂₉H₄₁NO₉
Molecular Weight:547.646
Hs Code.:

Synonyms:(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

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Chemical Property of (S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

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Technology Process of (S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

There total 15 articles about (S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate 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: 61.0%

: 1335286-86-6
(S)-2-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

: 1335286-87-7
(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
DOI:10.1016/j.tet.2011.08.014

Reference yield:

: 1135051-09-0
(2R,3S)-3-tert-butyldiphenylsilyloxy-4-penten-2-ol

: 1335286-87-7
(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: dmap / toluene / 1 h / 20 °C / Inert atmosphere

2.1: water; acetic acid / tetrahydrofuran / Inert atmosphere

3.1: dmap / toluene / 1 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

4.2: Inert atmosphere; Saturated solution

5.1: 2-picoline borane complex; acetic acid / methanol / 0 - 20 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere

With dmap; 2-picoline borane complex; tetrabutyl ammonium fluoride; water; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Yamaguchi reaction / 3.1: Yamaguchi reaction;
DOI:10.1016/j.tet.2011.08.014

Reference yield:

: 1174412-62-4
(3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene

: 1335286-87-7
(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: water; acetic acid / tetrahydrofuran / Inert atmosphere

2.1: dmap / toluene / 1 h / 20 °C / Inert atmosphere

3.1: water; acetic acid / tetrahydrofuran / Inert atmosphere

4.1: dmap / toluene / 1 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.2: Inert atmosphere; Saturated solution

6.1: 2-picoline borane complex; acetic acid / methanol / 0 - 20 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere

With dmap; 2-picoline borane complex; tetrabutyl ammonium fluoride; water; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 2.1: Yamaguchi reaction / 4.1: Yamaguchi reaction;
DOI:10.1016/j.tet.2011.08.014