(E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide

Base Information

• Chemical Name: (E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide
• CAS No.: 675832-23-2
• Molecular Formula: C₂₁H₂₇N₃O₆S₂
• Molecular Weight: 481.594
• Mol file: 675832-23-2.mol

Synonyms:(E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide

Chemical Property of (E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide

There total 5 articles about (E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-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: 82.0%

(RS)-O-(methoxymethyl)-S-((benzylthio)methyl)-D-cysteinol S-oxide (675832-21-0) + (E)-β-(2,4-Dioxo-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid (28277-67-0) → (E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide (675832-23-2)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1271/bbb.67.2556

Reference yield:

dibenzyl disulphide (150-60-7) → (E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide (675832-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 7 percent / lithium diisopropylamide / hexane; tetrahydrofuran / 0.5 h / 0 °C

2: 82 percent / dicyclohexyl carbodiimide; 1-hydroxy-7-azabenzotriazole / dimethylformamide / 12 h / 20 °C

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

DOI:10.1271/bbb.67.2556

Reference yield:

N-(benzyloxycarbonyl)-O-(methoxymethyl)-S-methyl-D-cysteinol (95407-08-2) → (E)-N-[(S)-2-((R)-Benzylsulfanylmethanesulfinyl)-1-methoxymethoxymethyl-ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acrylamide (675832-23-2)

Guidance literature:

Multi-step reaction with 4 steps

1: tert-butyl hydroperoxide; Ti(O-iPr)4; (S)-(-)-1,1'-bi-2-naphthol / CCl₄; H₂O; decane / 1 h / 20 °C

2: 91 percent / sodium; liq. ammonia / -78 °C

3: 7 percent / lithium diisopropylamide / hexane; tetrahydrofuran / 0.5 h / 0 °C

4: 82 percent / dicyclohexyl carbodiimide; 1-hydroxy-7-azabenzotriazole / dimethylformamide / 12 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 1-hydroxy-7-aza-benzotriazole; ammonia; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; decane; hexane; water; N,N-dimethyl-formamide;

DOI:10.1271/bbb.67.2556

upstream raw materials:

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

(E)-β-(2,4-Dioxo-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid

dibenzyl disulphide

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

Downstream raw materials:

benzylsparsomycin