3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

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Chemical Name:3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide
CAS No.:691012-82-5
Molecular Formula:C₅₀H₇₅ClINO₈Si₃
Molecular Weight:1064.76
Hs Code.:

3-(3-{1-[1,5-bis-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-<i>N</i>-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

Synonyms:3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

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Chemical Property of 3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

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Technology Process of 3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

There total 9 articles about 3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide 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: 77.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 691012-87-0
(R)-3-{2-Chloro-3-[(R)-1-((1S,5R)-2-ethynyl-1,5-dihydroxy-cyclopent-2-enyl)-prop-2-ynyloxy]-4-methoxy-phenyl}-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

: 691012-82-5
3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2004.02.020

Reference yield:

: 37687-57-3
2-chloro-3-hydroxy-4-methoxybenzaldehyde

: 691012-82-5
3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / imidazole / dimethylformamide / 0.75 h / 20 °C

2: 64 percent / stannous triflate; N-ethyl piperidine; chiral diamine / CH₂Cl₂ / 10 h / -95 °C

3: 88 percent / CH₂Cl₂ / 2 h / 20 °C

4: 85 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

5: 50 percent / CsF / dimethylformamide / 12 h / 60 °C

6: 77 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

With 1-ethyl-piperidine; 1H-imidazole; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; chiral diamine; tetrabutyl ammonium fluoride; cesium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: asymmetric Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2004.02.020

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 691012-82-5
3-(3-{1-[1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

Guidance literature:: Multi-step reaction with 8 steps

1: 60 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

2: 87 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

3: 98 percent / PPh₃; DEAD / tetrahydrofuran / 0.5 h / 20 °C

4: 99 percent / hydrazine monohydrate / tetrahydrofuran / 0.5 h / 20 °C

5: 88 percent / CH₂Cl₂ / 2 h / 20 °C

6: 85 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

7: 50 percent / CsF / dimethylformamide / 12 h / 60 °C

8: 77 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; sodium hydride; hydrazine hydrate; triphenylphosphine; cesium fluoride; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Mitsunobu reaction;
DOI:10.1016/j.tet.2004.02.020