3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester

Base Information

Chemical Name:3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester
CAS No.:878003-22-6
Molecular Formula:C₄₇H₇₀N₂O₉Si
Molecular Weight:835.166
Hs Code.:

3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester

Synonyms:3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester

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Chemical Property of 3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester

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Technology Process of 3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester

There total 23 articles about 3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid 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: 90.0%

: 1026590-77-1
(Z)-4-{(1S,2S,3aR,4S,6aS)-2-[(E)-4-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydro-pentalen-1-yl}-but-2-enal

: 878003-14-6
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-[2-(diethoxy-phosphoryl)-acetylamino]-2-(2,4-dimethoxy-benzylamino)-pentanoic acid ethyl ester

: 878003-22-6
3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester

Guidance literature:: (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-[2-(diethoxy-phosphoryl)-acetylamino]-2-(2,4-dimethoxy-benzylamino)-pentanoic acid ethyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.25h;

(Z)-4-{(1S,2S,3aR,4S,6aS)-2-[(E)-4-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydro-pentalen-1-yl}-but-2-enal; In tetrahydrofuran; at -78 - 20 ℃; for 0.5h;
DOI:10.1021/ja057899a

Reference yield:

: 5-tert-butoxycarbonylamino-2,3-dihydroxy-pentanoic acid ethyl ester

: 878003-22-6
3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: SOCl₂; Et₃N / CH₂Cl₂

1.2: NaN₃ / dimethylformamide / 55 °C

2.1: CH₂Cl₂

3.1: H₂ / Pd/C / ethyl acetate

4.1: 4 Angstroem molecular sieves / methanol

5.1: NaBH₃CN / methanol

6.1: TFA / CH₂Cl₂

7.1: thiazolidine-2-thione; EDCI; DMAP / Et₃N

8.1: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C

8.2: 90 percent / tetrahydrofuran / 0.5 h / -78 - 20 °C

With thiazolidine-2-thione; dmap; thionyl chloride; 4 A molecular sieve; hydrogen; sodium hexamethyldisilazane; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; triethylamine; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja057899a

Reference yield:

: 2-azido-5-tert-butoxycarbonylamino-3-hydroxy-pentanoic acid ethyl ester

: 878003-22-6
3-(tert-butyldimethylsilanyloxy)-2-(2,4-dimethoxybenzylamino)-5-(6-{2-[4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)but-1-enyl]-4-methyl-1,2,3,3a,4,6a-hexahydropentalen-1-yl}hexa-2,4-dienoylamino)pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: CH₂Cl₂

2.1: H₂ / Pd/C / ethyl acetate

3.1: 4 Angstroem molecular sieves / methanol

4.1: NaBH₃CN / methanol

5.1: TFA / CH₂Cl₂

6.1: thiazolidine-2-thione; EDCI; DMAP / Et₃N

7.1: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C

7.2: 90 percent / tetrahydrofuran / 0.5 h / -78 - 20 °C

With thiazolidine-2-thione; dmap; 4 A molecular sieve; hydrogen; sodium hexamethyldisilazane; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; triethylamine; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja057899a