(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-carbaldehyde

Base Information

Chemical Name:(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-carbaldehyde
CAS No.:220803-00-9
Molecular Formula:C₃₇H₄₈O₈SSi
Molecular Weight:680.935
Hs Code.:

(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-carbaldehyde

Synonyms:(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-carbaldehyde

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Chemical Property of (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-carbaldehyde

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Technology Process of (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-carbaldehyde

There total 16 articles about (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-carbaldehyde 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: 95.0%

: (3R,3aR,5S,6R,7S,7aS)-3-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxymethyl-5-(3-methoxy-benzyloxy)-7-(2-methoxy-ethoxymethoxy)-octahydro-benzo[b]thiophen-6-ol

: 220803-00-9
(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-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;
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

: 220803-00-9
(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-carbaldehyde

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; dmap; sodium sulfide; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; pyridinium p-toluenesulfonate; 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

: 220803-00-9
(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-carbaldehyde

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; dmap; sodium sulfide; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; pyridinium p-toluenesulfonate; 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