(2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

Base Information

Chemical Name:(2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide
CAS No.:471923-86-1
Molecular Formula:C₄₃H₆₁NO₇Si
Molecular Weight:732.045
Hs Code.:

(2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

Synonyms:(2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

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Chemical Property of (2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

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Technology Process of (2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

There total 27 articles about (2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide 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: 88.0%

: 471923-85-0
[[13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]heneicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-hexa-2,4-dienoyl-carbamic acid 2-trimethylsilanyl-ethyl ester

: 471923-86-1
(2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h;
DOI:10.1021/ja020635t

Reference yield:

: 110-44-1,5309-56-8,5309-57-9,22500-92-1,30361-30-9,91751-55-2
(2Z,4E)-hexa-2,4-dienoic acid

: 471923-86-1
(2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

1.2: (COCl)2 / tetrahydrofuran; hexane / 0 - 20 °C

2.1: NaHMDS / tetrahydrofuran / 0.38 h / -78 °C

2.2: 59 percent / tetrahydrofuran / -78 - 0 °C

3.1: 88 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; In tetrahydrofuran; hexane;
DOI:10.1021/ja020635t

Reference yield:

: 4423-18-1
(but-2-enylidene)malonic acid

: 471923-86-1
(2Z,4E)-Hexa-2,4-dienoic acid [(R)-[(2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-amide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 79 percent / quinoline / 3 h / 130 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

2.2: (COCl)2 / tetrahydrofuran; hexane / 0 - 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.38 h / -78 °C

3.2: 59 percent / tetrahydrofuran / -78 - 0 °C

4.1: 88 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

With quinoline; n-butyllithium; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; In tetrahydrofuran; hexane;
DOI:10.1021/ja020635t