6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one

Base Information

Chemical Name:6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one
CAS No.:220803-10-1
Molecular Formula:C₄₃H₅₄O₁₀SSi
Molecular Weight:791.047
Hs Code.:

6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one

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Chemical Property of 6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one

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Technology Process of 6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one

There total 19 articles about 6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one 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:

: 6-{[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophen-6-yl]-hydroxy-methyl}-3-methyl-2,3-dihydro-pyran-4-one

: 220803-10-1
6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; Yield given;
DOI:10.1016/S0040-4039(98)80004-X

Reference yield:

: Methanesulfonic acid (R)-2-[(1S,4R,5S)-4-hydroxy-5-(3-methoxy-benzyloxy)-cyclohex-2-enyl]-2-(4-methoxy-benzyloxy)-ethyl ester

: 220803-10-1
6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one

Guidance literature:: Multi-step reaction with 14 steps

1: 92 percent / m-CPBA / CH₂Cl₂ / -10 deg C -> r.t., 12 h

2: 93 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

3: 75 percent / tetrahydrofuran / 0 °C

4: 76 percent / NMO, OsO₄ / acetone; H₂O

5: 98 percent / PPTS / CH₂Cl₂

6: 85 percent / Na₂S*9H₂O / ethanol / 2 h / 60 °C

7: 98 percent / Huenig's base, DMAP / CH₂Cl₂ / 16 h

8: 68 percent / DDQ / CH₂Cl₂; H₂O / 0.33 h

9: imidazole / CH₂Cl₂

10: 85 percent / 80 percent AcOH / H₂O

11: 95 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

12: t-BuLi, HMPA / tetrahydrofuran / -78 -> 0 deg C

13: oxalic acid / H₂O; CH₂Cl₂ / 2 h / Ambient temperature

14: (COCl)2, DMSO, Et₃N / CH₂Cl₂

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium sulfide; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tert.-butyl lithium; pyridinium p-toluenesulfonate; oxalic acid; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;
DOI:10.1016/S0040-4039(98)80004-X

Reference yield:

: Methanesulfonic acid (R)-2-(4-methoxy-benzyloxy)-2-[(1R,2R,4S,6R)-4-(3-methoxy-benzyloxy)-5-oxo-7-oxa-bicyclo[4.1.0]hept-2-yl]-ethyl ester

: 220803-10-1
6-[(3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophene-6-carbonyl]-3-methyl-2,3-dihydro-pyran-4-one

Guidance literature:: Multi-step reaction with 12 steps

1: 75 percent / tetrahydrofuran / 0 °C

2: 76 percent / NMO, OsO₄ / acetone; H₂O

3: 98 percent / PPTS / CH₂Cl₂

4: 85 percent / Na₂S*9H₂O / ethanol / 2 h / 60 °C

5: 98 percent / Huenig's base, DMAP / CH₂Cl₂ / 16 h

6: 68 percent / DDQ / CH₂Cl₂; H₂O / 0.33 h

7: imidazole / CH₂Cl₂

8: 85 percent / 80 percent AcOH / H₂O

9: 95 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

10: t-BuLi, HMPA / tetrahydrofuran / -78 -> 0 deg C

11: oxalic acid / H₂O; CH₂Cl₂ / 2 h / Ambient temperature

12: (COCl)2, DMSO, Et₃N / CH₂Cl₂

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium sulfide; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tert.-butyl lithium; pyridinium p-toluenesulfonate; oxalic acid; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;
DOI:10.1016/S0040-4039(98)80004-X