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

Base Information

• Chemical Name: 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
• CAS No.: 173153-53-2
• Molecular Formula: C₃₅H₅₄N₄O₉SSi
• Molecular Weight: 734.987

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 14 articles about 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 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:

2-[(R)-2-[3-(Allyloxycarbonylamino-methyl)-[1,2,4]oxadiazol-5-yl]-2-(5-trityloxy-pentanoylamino)-ethylsulfanylmethyl]-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methoxy-6-methyl-benzoic acid allyl ester → 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 (173153-53-2)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 20 ℃; for 3h;

DOI:10.1021/jm0310232

Reference yield:

1 ,5-pentanediol (111-29-5) → 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 (173153-53-2)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; methanol; potassium permanganate; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; acetone; acetonitrile;

DOI:10.1021/jm0310232

Reference yield:

methyl 3,5-dimethoxy-2-methylbenzoate (52344-94-2) → 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 (173153-53-2)

Guidance literature:

Multi-step reaction with 8 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

With methanol; triethylsilane; potassium hydroxide; 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

upstream raw materials:

1 ,5-pentanediol

methyl 3,5-dimethoxy-2-methylbenzoate

chlorodimethyl(1,1,2-trimethylpropyl)silane

5-[(triphenylmethyl)oxy]pentanol

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

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