(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

Base Information

• Chemical Name: (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
• CAS No.: 850656-45-0
• Molecular Formula: C₄₁H₆₂O₈Si₂
• Molecular Weight: 739.109

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 23 articles about (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 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,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 (850656-45-0)

Guidance literature:

Multi-step reaction with 10 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

8.1: thexylborane / tetrahydrofuran / 0 - 20 °C

8.2: 76 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 1 h / 20 °C

9.1: 93 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

10.1: LHMDS; Et₃N / tetrahydrofuran / 1 h / -78 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; thexylborane; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hexamethyldisilazane; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 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,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 (850656-45-0)

Guidance literature:

Multi-step reaction with 11 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

9.1: thexylborane / tetrahydrofuran / 0 - 20 °C

9.2: 76 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 1 h / 20 °C

10.1: 93 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

11.1: LHMDS; Et₃N / tetrahydrofuran / 1 h / -78 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; pyridine-SO₃ complex; 4 A molecular sieve; thexylborane; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hexamethyldisilazane; potassium hexamethylsilazane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium hexamethyldisilazane; 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,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 (850656-45-0)

Guidance literature:

Multi-step reaction with 9 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

7.1: thexylborane / tetrahydrofuran / 0 - 20 °C

7.2: 76 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 1 h / 20 °C

8.1: 93 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

9.1: LHMDS; Et₃N / tetrahydrofuran / 1 h / -78 °C

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

DOI:10.1021/ja042686r

upstream raw materials:

(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

chloro-trimethyl-silane

(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:

C₃₉H₅₇IO₈Si

C₃₉H₅₈O₉Si

C₃₉H₅₆O₉Si

C₃₉H₅₆O₈Si

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