[[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

Base Information

• Chemical Name: [[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
• CAS No.: 471923-85-0
• Molecular Formula: C₄₉H₇₃NO₉Si₂
• Molecular Weight: 876.291
• Mol file: 471923-85-0.mol

Synonyms:[[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

Chemical Property of [[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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [[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

There total 25 articles about [[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 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: 59.0%

2(Z),4(E)-hexadienoic acid chloride (471924-12-6) + [(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]-carbamic acid 2-trimethylsilanyl-ethyl ester (471923-84-9) → [[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 (471923-85-0)

Guidance literature:

[(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]-carbamic acid 2-trimethylsilanyl-ethyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.383333h;

2(Z),4(E)-hexadienoic acid chloride; In tetrahydrofuran; at -78 - 0 ℃; Further stages.;

DOI:10.1021/ja020635t

Reference yield:

(2Z,4E)-hexa-2,4-dienoic acid (110-44-1,5309-56-8,5309-57-9,22500-92-1,30361-30-9,91751-55-2) → [[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 (471923-85-0)

Guidance literature:

Multi-step reaction with 2 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

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexane;

DOI:10.1021/ja020635t

Reference yield:

(but-2-enylidene)malonic acid (4423-18-1) → [[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 (471923-85-0)

Guidance literature:

Multi-step reaction with 3 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

With quinoline; n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexane;

DOI:10.1021/ja020635t

upstream raw materials:

2(Z),4(E)-hexadienoic acid chloride

[(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]-carbamic acid 2-trimethylsilanyl-ethyl ester

(2Z,4E)-hexa-2,4-dienoic acid

(but-2-enylidene)malonic acid

Downstream raw materials:

(2Z,4E)-Hexa-2,4-dienoic acid [(R)-((2E,8E,10Z,14E)-(1R,5S,13R,17R)-13-hydroxy-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

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

(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