(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

Base Information

Chemical Name:(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
CAS No.:173153-54-3
Molecular Formula:C₃₂H₅₀N₄O₉SSi
Molecular Weight:694.922
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 17 articles about (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 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:

: 2937-50-0
Allyl chloroformate

: 2-[(R)-2-(3-Aminomethyl-[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

: 173153-54-3
(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

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/jm0310232

Reference yield:

: 111-29-5
1 ,5-pentanediol

: 173153-54-3
(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

Guidance literature:: Multi-step reaction with 7 steps

1: 47 percent / pyridine / 16.5 h / 0 - 20 °C

2: 75 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1.33 h / -70 - 10 °C

3: 78 percent / aq. KMnO₄ / acetone / 2 h / 20 °C

4: EDC / acetonitrile / 0 °C

5: pTsOH*H₂O; MeOH / 3 h / 20 °C

6: 4-trimethylsilylmorpholine; trimethylsilyl acetate; Pd(PPh₃)4 / CH₂Cl₂ / 2 h / 20 °C

7: N-methylmorpholine / CH₂Cl₂ / 2 h / 0 °C

With 4-methyl-morpholine; pyridine; 4-(trimethylsilyl)morpholine; methanol; potassium permanganate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; trimethylsilyl acetate; toluene-4-sulfonic acid; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; acetone; acetonitrile;
DOI:10.1021/jm0310232

Reference yield:

: 52344-94-2
methyl 3,5-dimethoxy-2-methylbenzoate

: 173153-54-3
(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

Guidance literature:: Multi-step reaction with 10 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

7.1: EDC / acetonitrile / 0 °C

8.1: pTsOH*H₂O; MeOH / 3 h / 20 °C

9.1: 4-trimethylsilylmorpholine; trimethylsilyl acetate; Pd(PPh₃)4 / CH₂Cl₂ / 2 h / 20 °C

10.1: N-methylmorpholine / CH₂Cl₂ / 2 h / 0 °C

With 4-methyl-morpholine; 4-(trimethylsilyl)morpholine; methanol; triethylsilane; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl acetate; boron trichloride; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; trichlorophosphate; N,N,N',N'-tetramethylguanidine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Vilsmeyer formylation;
DOI:10.1021/jm0310232