[[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 Edit

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.:389123-28-8
Molecular Formula:C₄₉H₇₃NO₉Si₂
Molecular Weight:876.291
Hs Code.:
Mol file:389123-28-8.mol

[[13-(<i>tert</i>-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

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

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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 Edit

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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 33 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: 58.0%

: 471924-12-6
2(Z),4(E)-hexadienoic acid chloride

: 389123-27-7
[(S)-[(2E,8E,10Z,14E)-(1R,5R,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

: 389123-28-8
[[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

Guidance literature:: [(S)-[(2E,8E,10Z,14E)-(1R,5R,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 0.216667h;

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

: 389123-28-8
[[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

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 / 0.22 h / -78 °C

2.2: 58 percent / tetrahydrofuran; hexane / -78 - 0 °C

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

Reference yield:

: 197520-87-9
(R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate

: 389123-28-8
[[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

Guidance literature:: Multi-step reaction with 18 steps

1.1: CuI / tetrahydrofuran; diethyl ether / 0.17 h / 0 °C

1.2: 78 percent / tetrahydrofuran; diethyl ether / 1.17 h / -78 °C

2.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / -78 - 0 °C

3.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

4.1: 91 percent / 4,4'-di-tert-butylbiphenyl; Li / tetrahydrofuran / -78 °C

5.1: 97 percent / oxalyl chloride; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.2: 88 percent / tetrahydrofuran; toluene / -78 - 20 °C

7.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

7.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

7.3: 77 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

8.1: 94 percent / DCC; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 72 percent / HF*pyridine / tetrahydrofuran / 4.5 h / 20 °C

10.1: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

11.1: 72 percent / NaHMDS / tetrahydrofuran / -78 - 0 °C

12.1: 59 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 0 °C

13.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1.17 h / 20 °C

14.1: 20.6 mg / NaClO₂; sodium dihydrogenphosphate monohydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 1 h / 20 °C

15.1: N,N-diisopropylethylamine; i-BuOCOCl / acetone / 0.5 h / 0 °C

15.2: aq. NaN₃ / acetone / 1.5 h / 0 °C

16.1: toluene / 0.25 h / Heating

17.1: 24.5 mg / toluene / 3 h / Heating

18.1: NaHMDS / tetrahydrofuran / 0.22 h / -78 °C

18.2: 58 percent / tetrahydrofuran; hexane / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; oxalyl dichloride; 4,4'-di-tert-butylbiphenyl; water; tert.-butyl lithium; sodium hexamethyldisilazane; lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; pentane; 1.1: Michael addition / 5.1: Swern oxidation / 6.2: Julia olefination / 8.1: Mitsunobu reaction / 11.1: Horner-Wadsworth-Emmoms macrocyclization / 16.1: Curtius rearrangement;
DOI:10.1021/ja020635t