methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

Base Information

Chemical Name:methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate
CAS No.:496972-56-6
Molecular Formula:C₃₄H₃₆N₂O₇
Molecular Weight:584.669
Hs Code.:

methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

Synonyms:methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

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Chemical Property of methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

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Technology Process of methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

There total 5 articles about methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate 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: 72.0%

: 496972-55-5
methyl (1S,2R,3aS,6aR)-2-[(2S)-3-(4-tert-butoxyphenyl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoylamino]-5,5-(2',2'-dimethyltrimethylenedioxy)octahydropentalene-1-carboxylate

: 496972-56-6
methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

Guidance literature:: methyl (1S,2R,3aS,6aR)-2-[(2S)-3-(4-tert-butoxyphenyl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoylamino]-5,5-(2',2'-dimethyltrimethylenedioxy)octahydropentalene-1-carboxylate; With triethylsilane; trifluoroacetic acid; at 22 ℃; for 4.5h;

With silica gel; In ethanol; at 22 ℃; for 1h;
DOI:10.1055/s-2002-34378

Reference yield:

: 116949-06-5
C₁₅H₂₄O₅

: 496972-56-6
methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

2.1: 95 percent / NaN₃ / dimethylformamide / 8 h / 20 °C

3.1: 82 percent / H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 20 °C

4.1: 91 percent / TBTU; NNM / dimethylformamide / 1 h / 22 °C

5.1: aq. TFA; Et₃SiH / 4.5 h / 22 °C

5.2: 72 percent / SiO₂ / ethanol / 1 h / 22 °C

With triethylsilane; sodium azide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1055/s-2002-34378

Reference yield:

: 474434-30-5
(1R,2S,3R,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-azidobicyclo[3.3.0]octane-2-carboxylic acid methyl ester

: 496972-56-6
methyl (1S,2R,3aS,5R,6aR)-2-{[(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoyl]amino}-5-hydroxyoctahydropentalene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 20 °C

2.1: 91 percent / TBTU; NNM / dimethylformamide / 1 h / 22 °C

3.1: aq. TFA; Et₃SiH / 4.5 h / 22 °C

3.2: 72 percent / SiO₂ / ethanol / 1 h / 22 °C

With triethylsilane; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trifluoroacetic acid; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1055/s-2002-34378