methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

Base Information

Chemical Name:methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate
CAS No.:157425-65-5
Molecular Formula:C₂₉H₂₈N₂O₇Se
Molecular Weight:595.511
Hs Code.:

Synonyms:methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

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Chemical Property of methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

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Technology Process of methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

There total 10 articles about methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate 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: 21.0%

: methyl (5α,5aα,9aα)-(+/-)-6-(benzyloxycarbonyl)-3,4,5,5a,7,8,9,9a-octahydro-8,8-dimethoxy-4-oxo-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

: 157425-64-4
methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

: 157425-65-5
methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at -20 ℃;
DOI:10.1016/S0040-4039(00)77174-7

Reference yield:

: trans-(+/-)-1-(benzyloxycarbonyl)-2-<2-<3-bromo-5-(methoxycarbonyl)-1H-pyrrol-2-yl>-2-oxoethyl>-1,2,5,6-tetrahydro-5-hydroxypyridine

: 157425-65-5
methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 72 percent / trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / a) 0 deg C, 20 min, b) 20 deg C, 3 h

2: 11 percent / Pd(OAc)2, (o-tol)3P, Et₃N / acetonitrile / 26 h / 110 °C

3: 76 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / a) -20 deg C, 2 h, b) 0 deg C, 1.5 h

4: Et₃N / CH₂Cl₂ / a) 0 deg C, 10 min, b) 22 deg C, 1.5 h

5: 1 N Bu₄NF / tetrahydrofuran / 13 h / 0 - 22 °C

6: 48 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 - -10 °C

With palladium diacetate; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; tris-(o-tolyl)phosphine; In tetrahydrofuran; dichloromethane; cyclohexane; acetonitrile;
DOI:10.1248/cpb.44.67

Reference yield:

: trans-(+/-)-5-acetoxy-1-(benzyloxycarbonyl)-2-<2-<3-bromo-5-(methoxycarbonyl)-1H-pyrrol-2-yl>-2-oxoethyl>-1,2,5,6-tetrahydro-5-hydroxypyridine

: 157425-65-5
methyl 6-(benzyloxycarbonyl)-3,7,8,9-tetrahydro-4-hydroxy-8,8-dimethoxy-5-(phenylseleno)-6H-pyrrolo<3,2-f>quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / 1.5 percent K₂CO₃ / methanol / 2 h / 19 °C

2: 72 percent / trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / a) 0 deg C, 20 min, b) 20 deg C, 3 h

3: 11 percent / Pd(OAc)2, (o-tol)3P, Et₃N / acetonitrile / 26 h / 110 °C

4: 76 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / a) -20 deg C, 2 h, b) 0 deg C, 1.5 h

5: Et₃N / CH₂Cl₂ / a) 0 deg C, 10 min, b) 22 deg C, 1.5 h

6: 1 N Bu₄NF / tetrahydrofuran / 13 h / 0 - 22 °C

7: 48 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 - -10 °C

With palladium diacetate; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; tris-(o-tolyl)phosphine; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetonitrile;
DOI:10.1248/cpb.44.67