N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

Base Information

Chemical Name:N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester
CAS No.:870992-74-8
Molecular Formula:C₃₄H₃₃F₂N₃O₆
Molecular Weight:617.649
Hs Code.:

Synonyms:N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

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Chemical Property of N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

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Technology Process of N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

There total 16 articles about N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl 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: 77.0%

: 910642-53-4
N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroproline

: (2S,4R)-4-fluoroprolylglycine benzyl ester hydrochloride

: 870992-74-8
N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃; for 21h;
DOI:10.1021/ja054674r

Reference yield:

: 87691-27-8,946610-68-0
N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

: 870992-74-8
N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Cs₂CO₃ / dimethylformamide / 0 °C

1.2: 95 percent / dimethylformamide

2.1: 36 percent / morph-DAST / tetrahydrofuran / 48 h / -78 - 20 °C

3.1: 100 percent / H₂ / Pd/C / methanol / 18 h

4.1: 79 percent / iPr₂NEt; PyBOP / CH₂Cl₂

5.1: 100 percent / HCl / dioxane / 1 h

6.1: 77 percent / PyBroP; DIEA / CH₂Cl₂ / 21 h / 0 - 20 °C

With hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; caesium carbonate; N-ethyl-N,N-diisopropylamine; morpholinosulfur trifluoride; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja054674r

Reference yield:

: 132622-90-3
(2S,4S)-2-benzyl 1-tert-butyl 4-hydroxypyrrolidine-1,2-dicarboxylate

: 870992-74-8
N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 36 percent / morph-DAST / tetrahydrofuran / 48 h / -78 - 20 °C

2: 100 percent / H₂ / Pd/C / methanol / 18 h

3: 79 percent / iPr₂NEt; PyBOP / CH₂Cl₂

4: 100 percent / HCl / dioxane / 1 h

5: 77 percent / PyBroP; DIEA / CH₂Cl₂ / 21 h / 0 - 20 °C

With hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; morpholinosulfur trifluoride; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/ja054674r