(13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

Base Information

Chemical Name:(13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone
CAS No.:247186-25-0
Molecular Formula:C₃₆H₅₆N₄O₆Si
Molecular Weight:668.949
Hs Code.:

(13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

Synonyms:(13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

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Chemical Property of (13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

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Technology Process of (13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

There total 19 articles about (13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone 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: 47.0%

: 247186-24-9
hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid hexa-3,5-dienyl ester

: 247186-25-0
(13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; at 40 ℃;
DOI:10.1021/ja021327y

Reference yield: 47.0%

: 247186-24-9
hept-6-en-1-oyl-L-valine-L-(tert-butyldimethylsilyl)-meta-tyrosine-hexahydropyridazine-3S-carboxylic acid hexa-3,5-dienyl ester

: (13Z,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

: 247186-25-0
(13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 40 ℃;
DOI:10.1002/(SICI)1521-3773(19990816)38:16<2443::AID-ANIE2443>3.0.CO;2-B

Reference yield:

: 1700-31-8
3-benzyloxybenzyl bromide

: 247186-25-0
(13E,15E)-(3S,6S,21S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetraone

Guidance literature:: Multi-step reaction with 13 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: 62 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: 71 percent / aq. HCl / acetonitrile / 2 h / 20 °C

3.1: 8.85 g / tetrahydrofuran / -15 - 20 °C

4.1: 100 percent / aq. LiOH / tetrahydrofuran / 3 h / 0 °C

5.1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -10 °C

6.1: 780 mg / N-methylmorpholine / tetrahydrofuran / -10 - 20 °C

7.1: H₂ / 10 percent Pd/C / propan-2-ol / 5 h

8.1: 5.4 g / imidazole / dimethylformamide / 16 h / 40 °C

9.1: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

10.1: 2.98 g / tetrahydrofuran / 20 °C

11.1: Zn; aq. NH₄OAc / tetrahydrofuran / 20 °C

12.1: 230 mg / Ph₃P; diethylazodicarboxylate / tetrahydrofuran / 20 °C

13.1: 47 percent / (PCy)3Cl₂Ru=CHPh / CH₂Cl₂ / 40 °C

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; Grubbs catalyst first generation; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; ammonium acetate; hydrogen; triphenylphosphine; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 12.1: Mitsunobu reaction;
DOI:10.1021/ja021327y