{(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane

Base Information

• Chemical Name: {(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane
• CAS No.: 850656-43-8
• Molecular Formula: C₃₈H₅₄O₇Si
• Molecular Weight: 650.928

Synonyms:{(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane

Chemical Property of {(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Useful:

Technology Process of {(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane

There total 19 articles about {(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-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:

(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde (850656-94-9) → {(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane (850656-43-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

1.2: 209.1 mg / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

3.1: aq. HCl / tetrahydrofuran / 5 h / 40 - 60 °C

4.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.75 h / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 1.5 h / 20 °C

5.2: 1.95 g / DMAP / tetrahydrofuran; toluene / 0.5 h / Heating

6.1: 979.5 mg / KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.67 h / -78 °C

7.1: 9-BBN / tetrahydrofuran / 2.5 h / 0 °C

7.2: 1.111 g / Pd(PPh₃)4; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 9 h / 50 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hexamethyldisilazane; potassium hexamethylsilazane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene; tert-butyl alcohol; 1.2: Wittig reaction / 7.2: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ja042686r

Reference yield:

[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-methanol (850656-40-5) → {(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane (850656-43-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.25 h / 0 °C

2.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

2.2: 209.1 mg / tetrahydrofuran / 1 h / 0 °C

3.1: 99 percent / H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

4.1: aq. HCl / tetrahydrofuran / 5 h / 40 - 60 °C

5.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.75 h / 20 °C

6.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 1.5 h / 20 °C

6.2: 1.95 g / DMAP / tetrahydrofuran; toluene / 0.5 h / Heating

7.1: 979.5 mg / KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.67 h / -78 °C

8.1: 9-BBN / tetrahydrofuran / 2.5 h / 0 °C

8.2: 1.111 g / Pd(PPh₃)4; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 9 h / 50 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; pyridine-SO₃ complex; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hexamethyldisilazane; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol; 1.1: Swern oxidation / 2.2: Wittig reaction / 8.2: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ja042686r

Reference yield:

[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-2-((Z)-3-[1,3]dioxolan-2-yl-propenyl)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane (850656-41-6) → {(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy}-triethyl-silane (850656-43-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

2.1: aq. HCl / tetrahydrofuran / 5 h / 40 - 60 °C

3.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.75 h / 20 °C

4.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 1.5 h / 20 °C

4.2: 1.95 g / DMAP / tetrahydrofuran; toluene / 0.5 h / Heating

5.1: 979.5 mg / KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.67 h / -78 °C

6.1: 9-BBN / tetrahydrofuran / 2.5 h / 0 °C

6.2: 1.111 g / Pd(PPh₃)4; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 9 h / 50 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; hydrogen; potassium hexamethylsilazane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene; tert-butyl alcohol; 6.2: Suzuki-Miyaura cross-coupling;

DOI:10.1021/ja042686r

upstream raw materials:

Triethyl-((2R,4aR,7R,9aS)-6-methylene-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy)-silane

Phosphoric acid (2S,3aS,8aR)-2-(2-benzyloxy-ethyl)-2,3,3a,7,8,8a-hexahydro-furo[3,2-b]oxepin-5-yl ester diphenyl ester

(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one

(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

Downstream raw materials:

C₃₄H₅₆O₉Si

(2S,3aS,5R,8aR)-2-(2-Benzyloxy-ethyl)-5-((2R,4aR,6S,7R,9aS)-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-hexahydro-furo[3,2-b]oxepin-6-one

C₃₆H₆₀O₈SSi

(2R,4aR,6S,7R,9aS)-6-[(2S,3aS,5R,8aR)-2-(2-Benzyloxy-ethyl)-6-trimethylsilanyloxy-2,3,3a,5,8,8a-hexahydro-furo[3,2-b]oxepin-5-ylmethyl]-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocycloheptene

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