((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane

Base Information

Chemical Name:((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane
CAS No.:850657-00-0
Molecular Formula:C₄₁H₆₂O₇SSi
Molecular Weight:727.091
Hs Code.:

((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane

Synonyms:((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane

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Chemical Property of ((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane

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Technology Process of ((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane

There total 15 articles about ((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane 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: 81.0%

: 850656-89-2
(4aS,6R,8S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-8-triisopropylsilanyloxy-hexahydro-1,5-dioxa-benzocyclohepten-7-one

: 75-08-1
ethanethiol

: 850657-00-0
((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane

Guidance literature:: With zinc trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/ja042686r

Reference yield:

: (4aR,5aS,9aR,11aS)-2-(4-Methoxy-phenyl)-decahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cycloheptene

: 850657-00-0
((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane

Guidance literature:: Multi-step reaction with 12 steps

1.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 6 h / 0 °C

2.1: 85 percent / I₂; PPh₃; imidazole / benzene / 0.33 h / 20 °C

3.1: 95 percent / potassium t-butoxide / tetrahydrofuran / 0.25 h / 0 °C

4.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C

4.2: Pd(PPh₃)4; aq. NaHCO₃ / dimethylformamide; tetrahydrofuran / 19 h / 20 °C

5.1: BH₃*SMe₂ / tetrahydrofuran / 3 h / 20 °C

5.2: 338.0 mg / aq. H₂O₂; NaOH / tetrahydrofuran / 1 h / 20 °C

6.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 85 percent / DDQ; aq. phosphate buffer / CH₂Cl₂ / 1.5 h / 20 °C / pH 7

8.1: 82 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

9.1: LHMDS; Et₃N / tetrahydrofuran / 0.5 h / -78 °C

10.1: 181.8 mg / N-methylmorpholine-N-oxide; aq. OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 21 h / 20 °C

11.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

12.1: 81 percent / Zn(OTf)2 / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; tetrapropylammonium perruthennate; dimethylsulfide borane complex; 4 A molecular sieve; potassium tert-butylate; iodine; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol; benzene; 4.2: Suzuli-Miyaura cross-coupling;
DOI:10.1021/ja042686r

Reference yield:

: 850656-80-3
(4aS,7S,9aR)-7-(4-Methoxy-benzyloxy)-6-methylene-octahydro-1,5-dioxa-benzocycloheptene

: 850657-00-0
((4aS,5aR,6aS,8R,9S,10aR,11aS,12S,13aR)-9-Benzyloxy-8-benzyloxymethyl-11a-ethylsulfanyl-tetradecahydro-1,5,7,11-tetraoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-12-yloxy)-triisopropyl-silane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C

1.2: Pd(PPh₃)4; aq. NaHCO₃ / dimethylformamide; tetrahydrofuran / 19 h / 20 °C

2.1: BH₃*SMe₂ / tetrahydrofuran / 3 h / 20 °C

2.2: 338.0 mg / aq. H₂O₂; NaOH / tetrahydrofuran / 1 h / 20 °C

3.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 85 percent / DDQ; aq. phosphate buffer / CH₂Cl₂ / 1.5 h / 20 °C / pH 7

5.1: 82 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

6.1: LHMDS; Et₃N / tetrahydrofuran / 0.5 h / -78 °C

7.1: 181.8 mg / N-methylmorpholine-N-oxide; aq. OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 21 h / 20 °C

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

9.1: 81 percent / Zn(OTf)2 / CH₂Cl₂ / 12 h / 20 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; tetrapropylammonium perruthennate; dimethylsulfide borane complex; 4 A molecular sieve; zinc trifluoromethanesulfonate; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 1.2: Suzuli-Miyaura cross-coupling;
DOI:10.1021/ja042686r