1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol

Base Information

• Chemical Name: 1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol
• CAS No.: 187978-47-8
• Molecular Formula: C₂₇H₄₇NO₅Si
• Molecular Weight: 493.759

Synonyms:1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol

Chemical Property of 1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol

Chemical Property:

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Technology Process of 1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol

There total 3 articles about 1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol 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: 84.0%

tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester (2483-49-0) + 2‐{3‐[(O‐tert‐butyldimethylsilyl)hydroxy]‐1,1‐dimethylpropyl}‐3,5‐dimethylphenol (134098-64-9) → 1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol (187978-47-8)

Guidance literature:

With dmap; In dichloromethane; for 14h; Heating;

DOI:10.1021/jo961778z

Reference yield: 36.0%

L-N-Boc-Ala (15761-38-3) + 2‐{3‐[(O‐tert‐butyldimethylsilyl)hydroxy]‐1,1‐dimethylpropyl}‐3,5‐dimethylphenol (134098-64-9) → 1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol (187978-47-8)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1002/1521-4184(200106)334:6<209::AID-ARDP209>3.0.CO;2-Y

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol (187978-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

2: 84 percent / DMAP / CH₂Cl₂ / 14 h / Heating

With dmap; triethylamine; In dichloromethane;

DOI:10.1021/jo961778z

upstream raw materials:

tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester

2‐{3‐[(O‐tert‐butyldimethylsilyl)hydroxy]‐1,1‐dimethylpropyl}‐3,5‐dimethylphenol

L-N-Boc-Ala

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₅₂H₆₄Cl₃N₇O₁₃

(S)-2-[2-(2-{(S)-2-[(S)-2-{3-[2-((S)-2-tert-Butoxycarbonylamino-propionyloxy)-4,6-dimethyl-phenyl]-3-methyl-butyrylamino}-3-(1H-indol-3-yl)-propionylamino]-propionylamino}-acetylamino)-acetylamino]-succinic acid 4-benzyl ester

(S)-2-[2-(2-{(S)-2-[(S)-2-{3-[2-((S)-2-Amino-propionyloxy)-4,6-dimethyl-phenyl]-3-methyl-butyrylamino}-3-(1H-indol-3-yl)-propionylamino]-propionylamino}-acetylamino)-acetylamino]-succinic acid 4-benzyl ester

C₄₅H₅₃N₇O₁₀

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