(S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester
• CAS No.: 182201-54-3
• Molecular Formula: C₂₇H₄₇NO₇Si₂
• Molecular Weight: 553.844
• Mol file: 182201-54-3.mol

Synonyms:(S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

Chemical Property of (S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

There total 12 articles about (S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl 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:

(S)-methyl 2-amino-3-(3,5-bis((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)propanoate + Allyl chloroformate (2937-50-0) → (S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester (182201-54-3)

Guidance literature:

With pyridine; In dichloromethane; at 40 ℃; for 8h;

Reference yield:

(Z)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-acrylic acid methyl ester → (S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester (182201-54-3)

Guidance literature:

With Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-); hydrogen; at 23 ℃; for 16h; under 2280 Torr;

DOI:10.1021/ja962480t

Reference yield:

3,5-di-tert-butyldimethylsilyloxy-4-methoxybenzaldehyde (103929-82-4) → (S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester (182201-54-3)

Guidance literature:

Multi-step reaction with 4 steps

1: piperidine, acetic acid / benzene / 18 h / 23 °C

2: (PhO)2P(O)N₃, Et₃N, 4 Angstroem molecular sieves / toluene / 2 h / 70 °C

3: 1 h / 23 °C

4: H₂, Rh<(COD)-(R,R)-DIPAMP>(+)*BF₄(-) / 16 h / 23 °C / 2280 Torr

With piperidine; Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-); 4 A molecular sieve; diphenyl phosphoryl azide; hydrogen; acetic acid; triethylamine; In toluene; benzene;

DOI:10.1021/ja962480t

upstream raw materials:

3,5-di-tert-butyldimethylsilyloxy-4-methoxybenzaldehyde

2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester

L-tyrosine

Allyl chloroformate

Downstream raw materials:

C₅₀H₅₄F₃N₃O₁₂SSi

C₄₈H₅₀F₃N₃O₁₁SSi

C₄₄H₄₈F₃N₃O₁₀SSi

(1'R,6R,6aR,7R,13S,14R,16R)-5-(acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8-dihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinoline]-14-carbonitrile