3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Base Information

Chemical Name:3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester
CAS No.:728895-82-7
Molecular Formula:C₃₇H₅₂N₂O₈Si
Molecular Weight:680.914
Hs Code.:

3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Synonyms:3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

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Chemical Property of 3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

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Technology Process of 3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

There total 9 articles about 3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl 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: 80.0%

: 728895-76-9
3-Vinyl-benzoic acid (2S,8S,8aR)-2-hydroxy-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

: (2R,3S)-3-Allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoic acid

: 728895-82-7
3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Guidance literature:: With 4-pyrrolidin-1-ylpyridine; dacarbazine; In dichloromethane; for 24h;
DOI:10.1016/j.bmcl.2004.04.060

Reference yield:

: 135042-17-0
(2R,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

: 728895-82-7
3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 97 percent / imidazole / dimethylformamide

2: 100 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

3: 90 percent / SO₃*Py; Et₃N; DMSO / CH₂Cl₂ / 1 h / 0 °C

4: 80 percent / tetrahydrofuran / 4 h / -78 °C

5: 85 percent / Et₃N; DMAP / CH₂Cl₂

6: TFA / CH₂Cl₂ / 1 h / 0 °C

7: Et₃N; DMAP / CH₂Cl₂

8: 90 percent / Cl₂Ru=CHPh(PCy₃)2 / CH₂Cl₂

9: 75 percent / aq. K₂CO₃ / tetrahydrofuran / 1 h

10: 90 percent / DIC; DMAP / CH₂Cl₂ / 24 h

11: 80 percent / HF*Py / acetonitrile / 17 h

12: 80 percent / DIC; 4-pyrrolidin-1-ylpyridine / CH₂Cl₂ / 24 h

With 1H-imidazole; dmap; Grubbs catalyst first generation; lithium borohydride; pyridine-SO₃ complex; potassium carbonate; 4-pyrrolidin-1-ylpyridine; pyridine hydrogenfluoride; dimethyl sulfoxide; dacarbazine; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4: Grignard reaction;
DOI:10.1016/j.bmcl.2004.04.060

Reference yield:

: Acetic acid 1-((2R,4S)-4-triisopropylsilanyloxy-pyrrolidin-2-yl)-allyl ester

: 728895-82-7
3-Vinyl-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-allyloxycarbonylamino-5-methyl-2-triisopropylsilanyloxy-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N; DMAP / CH₂Cl₂

2: 90 percent / Cl₂Ru=CHPh(PCy₃)2 / CH₂Cl₂

3: 75 percent / aq. K₂CO₃ / tetrahydrofuran / 1 h

4: 90 percent / DIC; DMAP / CH₂Cl₂ / 24 h

5: 80 percent / HF*Py / acetonitrile / 17 h

6: 80 percent / DIC; 4-pyrrolidin-1-ylpyridine / CH₂Cl₂ / 24 h

With dmap; Grubbs catalyst first generation; potassium carbonate; 4-pyrrolidin-1-ylpyridine; pyridine hydrogenfluoride; dacarbazine; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/j.bmcl.2004.04.060