(E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide

Base Information

• Chemical Name: (E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide
• CAS No.: 220323-15-9
• Molecular Formula: C₁₆H₂₃NO₆S₂
• Molecular Weight: 389.494

Synonyms:(E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide

Chemical Property of (E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide

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Technology Process of (E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide

There total 2 articles about (E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide 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: 38.0%

caffeic acid (331-39-5,501-16-6) + (RS)-O-(methoxymethyl)-S-((methylthio)methyl)-D-cysteinol S-oxide (95407-13-9) → (E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide (220323-15-9)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0960-894X(98)00604-0

Reference yield:

(SS)-N-(benzyloxycarbonyl)-O-(methoxymethyl)-S-methyl-D-cysteinol S-oxide (95407-09-3) → (E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide (220323-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / NaNH₂ / -78 °C

2: 29 percent / LDA / tetrahydrofuran / 0 °C

3: 38 percent / 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzo-7-azatriazole / dimethylformamide / Ambient temperature

With 1-hydroxy-7-aza-benzotriazole; sodium amide; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(98)00604-0

Reference yield: 62.0%

(E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-methoxymethoxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide (220323-15-9) → (E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-1-hydroxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-acrylamide

Guidance literature:

With methanol; Dowex 50W; at 50 ℃;

DOI:10.1016/S0960-894X(98)00604-0

upstream raw materials:

caffeic acid

(R_S)-O-(methoxymethyl)-S-((methylthio)methyl)-D-cysteinol S-oxide

(S_S)-N-(benzyloxycarbonyl)-O-(methoxymethyl)-S-methyl-D-cysteinol S-oxide

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