(Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-one

Base Information

Chemical Name:(Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-one
CAS No.:204187-80-4
Molecular Formula:C₂₁H₂₈O₅S
Molecular Weight:392.516
Hs Code.:

Synonyms:(Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-one

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Technology Process of (Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-one

There total 5 articles about (Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-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: 63.0%

: 225092-60-4
(Z)-1-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-cyclotridec-3-enecarboxylic acid methyl ester

: 204187-80-4
(Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-one

Guidance literature:: With ammonium fluoride; tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Ambient temperature;
DOI:10.1021/ja973846k

Reference yield:

: 55362-80-6
9-bromononan-1-ol

: 204187-80-4
(Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-one

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / Dess-Martin periodinane

2: tetrahydrofuran / -78 - 20 °C

3: 68 percent / KH / dimethylformamide / 20 °C

4: 85 percent / Pd(PPh₃)4; dppe / tetrahydrofuran / 6 h / Heating

5: 63 percent / TBAF; NH₄F / tetrahydrofuran / 20 °C

With ammonium fluoride; tetrabutyl ammonium fluoride; potassium hydride; Dess-Martin periodane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Oxidation / 2: Cycloaddition / 3: Alkylation / 4: Cyclization / 5: desilylation;
DOI:10.1021/ja963795b

Reference yield:

: 187808-10-2
{2-[3-(8-bromooctyl)oxiranyl]allyloxy}-tert-butyldimethylsilane

: 204187-80-4
(Z)-12-Benzenesulfonyl-3-hydroxy-14-oxa-bicyclo[10.3.1]hexadec-1-en-13-one

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / KH / dimethylformamide / 20 °C

2: 85 percent / Pd(PPh₃)4; dppe / tetrahydrofuran / 6 h / Heating

3: 63 percent / TBAF; NH₄F / tetrahydrofuran / 20 °C

With ammonium fluoride; tetrabutyl ammonium fluoride; potassium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Alkylation / 2: Cyclization / 3: desilylation;
DOI:10.1021/ja963795b