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

Base Information

Chemical Name:(2S,3aS,5R,7S,8aR)-2-(2-Benzyloxy-ethyl)-5-((2R,4aR,6S,7R,9aS)-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-7-triisopropylsilanyloxy-hexahydro-furo[3,2-b]oxepin-6-one
CAS No.:850656-47-2
Molecular Formula:C₄₇H₇₄O₉Si₂
Molecular Weight:839.27
Hs Code.:

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

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

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

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

There total 25 articles about (2S,3aS,5R,7S,8aR)-2-(2-Benzyloxy-ethyl)-5-((2R,4aR,6S,7R,9aS)-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-7-triisopropylsilanyloxy-hexahydro-furo[3,2-b]oxepin-6-one 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: 82.0%

: (2S,3aS,5R,8aR)-2-(2-Benzyloxy-ethyl)-7-hydroxy-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

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

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

: 850656-47-2
(2S,3aS,5R,7S,8aR)-2-(2-Benzyloxy-ethyl)-5-((2R,4aR,6S,7R,9aS)-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-7-triisopropylsilanyloxy-hexahydro-furo[3,2-b]oxepin-6-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1021/ja042686r

Reference yield:

: 850656-94-9
(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

: 850656-47-2
(2S,3aS,5R,7S,8aR)-2-(2-Benzyloxy-ethyl)-5-((2R,4aR,6S,7R,9aS)-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-7-triisopropylsilanyloxy-hexahydro-furo[3,2-b]oxepin-6-one

Guidance literature:: Multi-step reaction with 12 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

11.1: 29.1 mg / N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 14 h / 20 °C

12.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 15 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; 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; water; ethyl acetate; toluene; tert-butyl alcohol; 1.2: Wittig reaction / 7.2: Suzuki-Miyaura cross-coupling / 11.1: Rubbotom-type oxidation;
DOI:10.1021/ja042686r

Reference yield:

: 850656-40-5
[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-methanol

: 850656-47-2
(2S,3aS,5R,7S,8aR)-2-(2-Benzyloxy-ethyl)-5-((2R,4aR,6S,7R,9aS)-2-phenyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl)-7-triisopropylsilanyloxy-hexahydro-furo[3,2-b]oxepin-6-one

Guidance literature:: Multi-step reaction with 13 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

12.1: 29.1 mg / N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 14 h / 20 °C

13.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 15 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; 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; water; ethyl acetate; toluene; tert-butyl alcohol; 1.1: Swern oxidation / 2.2: Wittig reaction / 8.2: Suzuki-Miyaura cross-coupling / 12.1: Rubbotom-type oxidation;
DOI:10.1021/ja042686r