(2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Base Information

Chemical Name:(2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate
CAS No.:1443157-60-5
Molecular Formula:C₂₉H₃₄F₂O₈
Molecular Weight:548.581
Hs Code.:

(2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Synonyms:(2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

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Chemical Property of (2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

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Technology Process of (2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

There total 3 articles about (2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate 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: 44.0%

: 1443157-40-1
(2aR,4R,4aR,6S,11S,12S,12aR,12bS)-12b-acetoxy-4,6-difluoro-11-hydroxy-4a,8,13,13-tetramethyl-5,9-dioxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

: 1443157-60-5
(2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; Inert atmosphere;
DOI:10.1039/c3ob40654g

Reference yield:

: (2aR,4R,4aR,8R,11S,12S,12aR,12bS,Z)-12b-acetoxy-4-fluoro-11-hydroxy-4a,8,13,13-tetramethyl-5,9-dioxo-2a,3,4,4a,5,8,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

: 1443157-60-5
(2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hexamethylsilazane / toluene / -78 °C / Molecular sieve; Inert atmosphere

1.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0 °C / Inert atmosphere

With sodium tetrahydroborate; potassium hexamethylsilazane; In tetrahydrofuran; methanol; toluene;
DOI:10.1039/c3ob40654g

Reference yield:

: 32981-86-5,172018-16-5
10-deacetylbaccatin III

: 1443157-60-5
(2aR,4S,4aS,8S,9R,10S,11S,12S,12aR,12bS,E)-12b-acetoxy-8,10-difluoro-9,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-((triethylsilyl)oxy)-2a,3,4,4a,5,8,9,10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diethylamino-sulfur trifluoride / tetrahydrofuran / -78 °C / Molecular sieve; Inert atmosphere

2.1: potassium hexamethylsilazane / toluene / -78 °C / Molecular sieve; Inert atmosphere

2.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

3.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0 °C / Inert atmosphere

With sodium tetrahydroborate; diethylamino-sulfur trifluoride; potassium hexamethylsilazane; In tetrahydrofuran; methanol; toluene;
DOI:10.1039/c3ob40654g