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

Base Information

• Chemical Name: (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxyethoxy)methoxy-1-methyl-3-butenyl (S)-3-tert-butoxycarbonylamino-butenoate
• CAS No.: 1335286-49-1
• Molecular Formula: C₄₀H₅₉NO₁₀Si
• Molecular Weight: 741.995
• Mol file: 1335286-49-1.mol

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

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

There total 17 articles about (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxyethoxy)methoxy-1-methyl-3-butenyl (S)-3-tert-butoxycarbonylamino-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: 100.0%

(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl (2E,4R,5S)-5-hydroxy-4-(2-methoxyethoxy)methoxy-2-hexenoate (1335286-48-0) + (S)-3-tert-butoxycarbonylaminobutyric acid (158851-30-0) → (1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxyethoxy)methoxy-1-methyl-3-butenyl (S)-3-tert-butoxycarbonylamino-butenoate (1335286-49-1)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; Inert atmosphere;

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-(methoxyethoxy)methoxy-1-methyl-3-butenyl (S)-3-tert-butoxycarbonylamino-butenoate (1335286-49-1)

Guidance literature:

Multi-step reaction with 8 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

With methanol; dmap; ammonia; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene; 6.1: Yamaguchi reaction;

DOI:10.1016/j.tet.2011.08.014

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-(methoxyethoxy)methoxy-1-methyl-3-butenyl (S)-3-tert-butoxycarbonylamino-butenoate (1335286-49-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: water; acetic acid / tetrahydrofuran / Inert atmosphere

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

With dmap; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; toluene; 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-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate

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

(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