allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate

Base Information

• Chemical Name: allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate
• CAS No.: 173153-52-1
• Molecular Formula: C₃₀H₄₆N₄O₇SSi
• Molecular Weight: 634.869
• Mol file: 173153-52-1.mol

Synonyms:allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate

Chemical Property of allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate

There total 8 articles about allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate 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: 64.0%

(R)-2-mercapto-1-(3-allyloxycarbonylaminomethyl-1,2,4-oxadiazol-5-yl)ethylcarbamic acid tert-butyl ester (173153-51-0) + allyl 2-formyl-5-methoxy-6-methyl-3-(dimethyl(thexyl)silyloxy)benzoate (173152-59-5) → allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate (173153-52-1)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 18h;

DOI:10.1021/jm0310232

Reference yield:

methyl 3,5-dimethoxy-2-methylbenzoate (52344-94-2) → allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate (173153-52-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / POCl₃ / CH₂Cl₂ / 72 h / 40 °C

2.1: 86 percent / BCl₃ / CH₂Cl₂ / 4.5 h / 20 °C

3.1: 98 percent / aq. KOH / 0.5 h / 75 °C

4.1: N,N,N',N'-tetramethylguanidine / dimethylformamide / 0.5 h

4.2: 86 percent / dimethylformamide / 3 h

5.1: 90 percent / Et₃N / dimethylformamide / 6 h

6.1: 64 percent / TFA; Et₃SiH / CH₂Cl₂ / 18 h / 0 °C

With triethylsilane; potassium hydroxide; boron trichloride; triethylamine; trifluoroacetic acid; trichlorophosphate; N,N,N',N'-tetramethylguanidine; In dichloromethane; N,N-dimethyl-formamide; 1.1: Vilsmeyer formylation;

DOI:10.1021/jm0310232

Reference yield:

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-amino-ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate (173153-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₃N / dimethylformamide / 6 h

2: 64 percent / TFA; Et₃SiH / CH₂Cl₂ / 18 h / 0 °C

With triethylsilane; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0310232

upstream raw materials:

(R)-2-mercapto-1-(3-allyloxycarbonylaminomethyl-1,2,4-oxadiazol-5-yl)ethylcarbamic acid tert-butyl ester

allyl 2-formyl-5-methoxy-6-methyl-3-(dimethyl(thexyl)silyloxy)benzoate

methyl 3,5-dimethoxy-2-methylbenzoate

chlorodimethyl(1,1,2-trimethylpropyl)silane

Downstream raw materials:

(R)-2-[2-(3-allyloxycarbonylaminomethyl-1,2,4-oxadiazol-5-yl)-2-(5-hydroxy-pentanoylamino)-ethylsulfanylmethyl]-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methoxy-6-methyl-benzoic acid

2-[(R)-2-[3-(Allyloxycarbonylamino-methyl)-[1,2,4]oxadiazol-5-yl]-2-(5-hydroxy-pentanoylamino)-ethylsulfanylmethyl]-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methoxy-6-methyl-benzoic acid allyl ester

allyl 2-{(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyrylamino]ethylsulfanylmethyl}-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate

allyl 2-[(R)-2-[3-(allyloxycarbonylaminomethyl)-1,2,4-oxadiazol-5-yl]-2-((R)-5-hydroxy-6-trityloxyhexanoylamino)ethylsulfanylmethyl]-3-[dimethyl(thexyl)silyloxy]-5-methoxy-6-methylbenzoate