N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether

Base Information

Chemical Name:N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether
CAS No.:618460-96-1
Molecular Formula:C₄₃H₇₅NO₇Si₄
Molecular Weight:830.413
Hs Code.:

Synonyms:N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether

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Chemical Property of N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether

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Technology Process of N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether

There total 3 articles about N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether 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: 33.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 618460-38-1
D-clovamide methyl ester

: 618460-96-1
N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether

Guidance literature:: With triethylamine; In dichloromethane; for 18h;

Reference yield:

: 5796-17-8,90638-38-3
D-Dopa

: 618460-96-1
N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether

Guidance literature:: Multi-step reaction with 4 steps

1: SOCl₂ / 0 °C

2: 87 percent / PyBOP; TEA / CH₂Cl₂

3: BBr₃ / CH₂Cl₂

4: TEA / CH₂Cl₂

With thionyl chloride; TEA; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; boron tribromide; In dichloromethane;
DOI:10.1016/S0960-894X(03)00735-2

Reference yield:

: 71855-43-1
(R)-(3,4-dihydroxyphenyl)alanine methyl ester

: 618460-96-1
N-(3',4'-dihydroxy-trans-cinamoyl)-3-(3,4-dihydroxylphenyl)-D-alanine methyl ester tetra (t-butyldimethylsilyl)ether

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / PyBOP; TEA / CH₂Cl₂

2: BBr₃ / CH₂Cl₂

3: TEA / CH₂Cl₂

With TEA; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; boron tribromide; In dichloromethane;
DOI:10.1016/S0960-894X(03)00735-2