3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Base Information

Chemical Name:3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester
CAS No.:728895-54-3
Molecular Formula:C₂₈H₃₆N₂O₉
Molecular Weight:544.602
Hs Code.:

3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Synonyms:3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

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Chemical Property of 3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

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Technology Process of 3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

There total 10 articles about 3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-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: 86.0%

: 728895-90-7
(4S,5R)-2-(4-Methoxy-phenyl)-4-(2-methyl-propenyl)-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-[(2S,8S,8aR)-8-(3-methoxy-benzoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-2-yl] ester

: 728895-54-3
3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Guidance literature:: With toluene-4-sulfonic acid; In methanol;
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

: 728895-54-3
3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Guidance literature:: Multi-step reaction with 13 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: DIC; DMAP / CH₂Cl₂ / 24 h

11: HF*Py / acetonitrile

12: 96 percent / EDC*HCl; DMAP / CH₂Cl₂ / 24 h

13: 86 percent / p-TSA / methanol

With 1H-imidazole; dmap; Grubbs catalyst first generation; lithium borohydride; pyridine-SO₃ complex; potassium carbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dimethyl sulfoxide; dacarbazine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; 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

: 728895-54-3
3-Methoxy-benzoic acid (2S,8S,8aR)-2-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-5-methyl-hex-4-enoyloxy)-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-8-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N; DMAP / CH₂Cl₂

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

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

4: DIC; DMAP / CH₂Cl₂ / 24 h

5: HF*Py / acetonitrile

6: 96 percent / EDC*HCl; DMAP / CH₂Cl₂ / 24 h

7: 86 percent / p-TSA / methanol

With dmap; Grubbs catalyst first generation; potassium carbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dacarbazine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.bmcl.2004.04.060