(1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate

Base Information

• Chemical Name: (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate
• CAS No.: 1335287-11-0
• Molecular Formula: C₄₂H₅₇NO₈Si
• Molecular Weight: 732.002
• Mol file: 1335287-11-0.mol

Synonyms:(1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate

Chemical Property of (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate

There total 13 articles about (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate 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:

(2R,3S)-3-tert-butyldiphenylsilyloxy-4-penten-2-ol (1135051-09-0) → (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate (1335287-11-0)

Guidance literature:

Multi-step reaction with 5 steps

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

2.1: water; acetic acid / tetrahydrofuran / Inert atmosphere

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °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 / 0.5 h / 0 - 20 °C / Inert atmosphere

With dmap; 2-picoline borane complex; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Yamaguchi reaction;

DOI:10.1016/j.tet.2011.08.014

Reference yield:

ethyl (2E,4S,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-2-hexenoate → (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate (1335287-11-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triphenylphosphine; diethylazodicarboxylate / toluene; benzene / 2 h / 0 - 20 °C / Inert atmosphere

2.1: methanol; ammonia / water / 3 h / 0 - 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydroxide / tetrahydrofuran; methanol; water / 2 h / 0 - 20 °C

4.2: pH 3 - 4

5.1: triethylamine / toluene / 0.5 h / 0 °C / Inert atmosphere

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

7.1: water; acetic acid / tetrahydrofuran / Inert atmosphere

8.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere

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

9.2: Inert atmosphere; Saturated solution

10.1: 2-picoline borane complex; acetic acid / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere

With methanol; dmap; 2-picoline borane complex; ammonia; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene; 6.1: 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) → (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate (1335287-11-0)

Guidance literature:

Multi-step reaction with 6 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; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °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 / 0.5 h / 0 - 20 °C / Inert atmosphere

With dmap; 2-picoline borane complex; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 2.1: 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

(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl (2E,4R,5S)-5-tert-butyldimethylsilyloxy-4-(2-methoxyethoxy)methoxy-2-hexenoate

(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl (2E,4R,5S)-5-hydroxy-4-(2-methoxyethoxy)methoxy-2-hexenoate

Downstream raw materials:

(1S,2R,3E)-4-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-(acryloylbenzylamino)-butenoate

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

C₂₃H₂₉NO₇

C₂₃H₂₅NO₇