2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 338974-75-7
• Molecular Formula: C₃₇H₅₆N₂O₁₃
• Molecular Weight: 736.857
• Mol file: 338974-75-7.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester

There total 4 articles about 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl 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: 64.0%

Boc-Tyr-OH (3978-80-1) + 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-((R)-amino-methoxycarbonyl-methyl)-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester (338974-71-3) → 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester (338974-75-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 18h;

DOI:10.1016/S0960-894X(01)00039-7

Reference yield:

2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-bromo-3,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-4-yl ester (338974-69-9) → 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester (338974-75-7)

Guidance literature:

Multi-step reaction with 3 steps

1: ZnBr₂ / 1,2-dichloro-ethane / 18 h / Heating

2: 85 percent / NaBH₄ / methanol / 1.5 h / 0 - 20 °C

3: 64 percent / 1-hydroxybenzotriazole; EDAC; N(iPr)2Et / dimethylformamide / 18 h

With sodium tetrahydroborate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; zinc dibromide; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00039-7

Reference yield:

tetrapivaloyl-α-L(+)-arabinose → 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-{(R)-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methoxycarbonyl-methyl}-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester (338974-75-7)

Guidance literature:

Multi-step reaction with 4 steps

1: HBr; AcOH

2: ZnBr₂ / 1,2-dichloro-ethane / 18 h / Heating

3: 85 percent / NaBH₄ / methanol / 1.5 h / 0 - 20 °C

4: 64 percent / 1-hydroxybenzotriazole; EDAC; N(iPr)2Et / dimethylformamide / 18 h

With sodium tetrahydroborate; hydrogen bromide; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; zinc dibromide; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00039-7

upstream raw materials:

Boc-Tyr-OH

2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-2-((R)-amino-methoxycarbonyl-methyl)-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester

2,2-Dimethyl-propionic acid (2R,3R,4S,5S)-2-bromo-3,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-4-yl ester

2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4,5-bis-(2,2-dimethyl-propionyloxy)-2-[(R)-methoxycarbonyl-(2,2,2-trifluoro-acetylamino)-methyl]-tetrahydro-pyran-3-yl ester