2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester
• CAS No.: 154857-64-4
• Molecular Formula: C₂₉H₃₃N₃O₅
• Molecular Weight: 503.598
• Mol file: 154857-64-4.mol

Synonyms:2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester

There total 1 articles about 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl 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:

pivaloyl chloride (3282-30-2) + {(2R,3R)-3-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-oxiranyl}-methanol (139886-83-2) → 2,2-Dimethyl-propionic acid (2S,3S)-2-azido-3-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester + 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester (154857-64-4)

Guidance literature:

With pyridine; diisopropoxytitanium diazide; Multistep reaction. Yields of byproduct given; 1.) benzene, 2.) 30 min;

DOI:10.1248/cpb.41.1534

Reference yield: 86.0%

chloromethyl methyl ether (107-30-2) + 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester (154857-64-4) → 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-methoxymethoxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester (154857-65-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 4h; Heating;

DOI:10.1248/cpb.41.1534

Reference yield:

2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester (154857-64-4) → 2,2,2-Trifluoro-N-{(3E,7Z)-(1S,2R)-2-methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-heptadeca-3,7-dienyl}-acetamide

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / Heating

2: LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

3: Et₃N / methanol / 0.17 h / Ambient temperature

4: molecular sieves 4A, pyridinium dichromate / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 1.) n-butyllithium / 1.) THF, n-hexane, RT, 30 min, 2.) THF, n-hexane, -78 deg C, 1 h

6: H₂ / 5percent Pd/CaCO₃/quinoline / hexane / 2 h / Ambient temperature

With lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 4 A molecular sieve; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; quinoline; Lindlar's catalyst; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1248/cpb.41.1534

upstream raw materials:

pivaloyl chloride

{(2R,3R)-3-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-oxiranyl}-methanol

Downstream raw materials:

2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-methoxymethoxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butyl ester

(2S,3S)-3-Amino-2-methoxymethoxy-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-butan-1-ol

2,2,2-Trifluoro-N-{(1S,2S)-3-hydroxy-2-methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-propyl}-acetamide