(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-phenethylamino)-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-phenethylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate
• CAS No.: 1335286-92-4
• Molecular Formula: C₃₀H₄₃NO₉
• Molecular Weight: 561.673
• Mol file: 1335286-92-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-phenethylamino)-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-phenethylamino)-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: 62.0%

(S)-2-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-phenethylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate (1335286-91-3) → (S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-phenethylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate (1335286-92-4)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.08.014

Reference yield:

(2R,3S)-3-tert-butyldiphenylsilyloxy-4-penten-2-ol (1135051-09-0) → (S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-phenethylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate (1335286-92-4)

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:

(3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene (1174412-62-4) → (S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-phenethylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate (1335286-92-4)

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

upstream raw materials:

(2R,3S)-3-tert-butyldiphenylsilyloxy-4-penten-2-ol

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

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

(S)-2-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-tert-butoxycarbonylamino-4-(2-methoxyethoxy)methoxy-2-hexenoate

Downstream raw materials:

(3S,6E,8R,9S,12E,14R,15S)-14-hydroxy-8-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-10-phenethyl-10-aza-4,16-dioxa-6,12-cyclohexadecadiene-1,5,11-trione

C₂₄H₃₁NO₇

C₂₄H₂₇NO₇