(4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Base Information

Chemical Name:(4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol
CAS No.:850656-99-4
Molecular Formula:C₃₆H₅₄O₇Si
Molecular Weight:626.906
Hs Code.:

(4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Synonyms:(4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

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Chemical Property of (4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

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Technology Process of (4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

There total 10 articles about (4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol 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: 85.0%

: 850656-98-3
{(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-[(4aS,6R,7S,9aR)-7-(4-methoxy-benzyloxy)-octahydro-1,5-dioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-triethyl-silane

: 850656-99-4
(4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: With phosphate buffer; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 1.5h; pH=7;
DOI:10.1021/ja042686r

Reference yield:

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

: 850656-99-4
(4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; dimethylsulfide borane complex; potassium tert-butylate; iodine; diisobutylaluminium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; 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

: 850656-99-4
(4aS,6R,7S,9aR)-6-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 4 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

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; dimethylsulfide borane complex; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 1.2: Suzuli-Miyaura cross-coupling;
DOI:10.1021/ja042686r