Technology Process of (2S,5S,8S,11S,13aR)-5-Benzyl-11-[(R)-7-(tert-butyl-diphenyl-silanyloxy)-6-oxo-octyl]-8-ethyl-2,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone
There total 24 articles about (2S,5S,8S,11S,13aR)-5-Benzyl-11-[(R)-7-(tert-butyl-diphenyl-silanyloxy)-6-oxo-octyl]-8-ethyl-2,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-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:
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![(2S,5S,8S,11S,13aR)-5-Benzyl-11-[(R)-7-(tert-butyl-diphenyl-silanyloxy)-6-oxo-octyl]-8-ethyl-2,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone](/Databaselist/images/loading.webp)
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857478-39-8
(2S,5S,8S,11S,13aR)-5-Benzyl-11-[(R)-7-(tert-butyl-diphenyl-silanyloxy)-6-oxo-octyl]-8-ethyl-2,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone
- Guidance literature:
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(2R,4S)-1-((S)-2-{(S)-2-[(2S,9R)-2-tert-Butoxycarbonylamino-9-(tert-butyl-diphenyl-silanyloxy)-8-oxo-decanoylamino]-2-methyl-butyrylamino}-3-phenyl-propionyl)-4-methyl-pyrrolidine-2-carboxylic acid pentafluorophenyl ester;
With
trifluoroacetic acid;
In
dichloromethane;
for 1h;
With
sodium hydrogencarbonate;
In
chloroform; water;
for 24h;
DOI:10.1021/ol050991r
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857478-39-8
(2S,5S,8S,11S,13aR)-5-Benzyl-11-[(R)-7-(tert-butyl-diphenyl-silanyloxy)-6-oxo-octyl]-8-ethyl-2,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: LiOH / tetrahydrofuran; H2O
2.1: 2.91 g / EDC; DIPEA / CH2Cl2
3.1: Mg
3.2: 89 percent / tetrahydrofuran / 3 h / 20 °C
4.1: 55 percent / second-generation Grubbs RCM catalyst / 1,2-dichloro-ethane / 168 h / 20 °C
5.1: 94 percent / H2 / Pd/C / methanol / 6 h / 760 Torr
6.1: 78 percent / HOBt; EDCI; i-Pr2NEt / CH2Cl2 / 24 h / 20 °C
7.1: H2 / Pd/C / methanol / 6 h / 760 Torr
8.1: 149 mg / EDC / CH2Cl2
9.1: TFA / CH2Cl2 / 1 h
9.2: 56 percent / NaHCO3 / CHCl3; H2O / 24 h
With
lithium hydroxide; hydrogen; benzotriazol-1-ol; magnesium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane;
3.2: Grignard reaction;
DOI:10.1021/ol050991r
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857478-39-8
(2S,5S,8S,11S,13aR)-5-Benzyl-11-[(R)-7-(tert-butyl-diphenyl-silanyloxy)-6-oxo-octyl]-8-ethyl-2,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: TFA / CH2Cl2 / 0.5 h
1.2: 69 percent / EDCI; HOBt; i-Pr2NEt / CH2Cl2
2.1: diethylamine / acetonitrile / 0.5 h
3.1: 78 percent / HOBt; EDCI; i-Pr2NEt / CH2Cl2 / 24 h / 20 °C
4.1: H2 / Pd/C / methanol / 6 h / 760 Torr
5.1: 149 mg / EDC / CH2Cl2
6.1: TFA / CH2Cl2 / 1 h
6.2: 56 percent / NaHCO3 / CHCl3; H2O / 24 h
With
hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
methanol; dichloromethane; acetonitrile;
DOI:10.1021/ol050991r
