193693-68-4

Basic information

• Product Name: Fmoc-Nip-OH
• Synonyms: (2S,3'S)-1-(3-Methyl-2-MethylaMino-butyl)-pyrrolidin-3-ol 2HCl;(3S)-1,3-Piperidinedicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester;(S)-1,3-Piperidinedicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester;Fmoc-L-nipecotic acid;(S)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)piperidine-3-carboxylic acid;1,3-Piperidinedicarboxylic acid, 1-(9H-fluoren-9-ylmethyl) ester, (3S)-;Fmoc-L-Nip-OH;(3S)-1-Fmoc-3-piperidinecarboxylic acid
• CAS NO: 193693-68-4
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.4
• EINECS: 604-604-1
• Mol File: 193693-68-4.mol

Chemical Properties

• Melting Point: 160-161℃
• Boiling Point: 561.6°Cat760mmHg
• Flash Point: 293.5°C
• Appearance: /
• Density: 1.293
• Vapor Pressure: 1.89E-13mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: 2-8°C
• PKA: 4.47±0.20(Predicted)
• CAS DataBase Reference: Fmoc-Nip-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-Nip-OH(193693-68-4)
• EPA Substance Registry System: Fmoc-Nip-OH(193693-68-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 193693-68-4(Hazardous Substances Data)

Usage

Chemical Properties

White fine crystalline powder

InChI:InChI=1/C21H21NO4/c23-20(24)14-6-5-11-22(12-14)21(25)26-13-19-17-9-3-1-7-15(17)16-8-2-4-10-18(16)19/h1-4,7-10,14,19H,5-6,11-13H2,(H,23,24)/t14-/m0/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 498-95-3 nipecotic acid 
• 498-95-3 (S)-nipecotic acid 
• 637337-43-0 (4R)-3-(5-bromo-1-oxopentyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 88466-74-4 (3S)-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid 
• 4509-90-4 5-bromovaleroyl chloride 

Relevant articles and documents

Preparation of β2-amino acid derivatives (β2hThr, β2hTrp, β2hMet, β2hPro, β2hLys, pyrrolidine-3-carboxylic acid) by using DIOZ as chiral auxiliary

The title compounds were prepared from valine-derived N-acylated oxazolidin-2-ones, 1-3, 7, 9, by highly diastereoselective (≥ 90%) Mannich reaction (→ 4-6; Scheme 1) or aldol addition (→ 8 and 10; Scheme 2) of the corresponding Ti- or B-enolates as the key step. The superiority of the '5,5-diphenyl-4-isopropyl-1,3-oxazolidin-2-one' (DIOZ) was demonstrated, once more, in these reactions and in subsequent transformations leading to various t-Bu-, Boc-, Fmoc-, and Cbz-protected β2-homoamino acid derivatives 11-23 (Schemes 3-6). The use of ω-bromo-acyl-oxazolidinones 1-3 as starting materials turned out to open access to a variety of enantiomerically pure trifunctional and cyclic carboxylic-acid derivatives.

Catalysis with phosphine-containing amino acids in various "turn" motifs

We have been actively involved in the development of parallel approaches for the discovery of phosphine ligands. Our approach has been based on the incorporation of phosphine-containing amino acids into peptide sequences that are designed to have stable secondary structures. We have examined helical and turn secondary structures and have reported that alkylation of cyclopentenyl acetate with dimethylmalonate can be catalyzed in high enantiomeric excess (ee) with a β-turn-based ligand. The importance of the peptide secondary structure was demonstrated through the synthesis of a series of peptide ligands where the nature of the turn-forming residues was probed. Additionally, other turn-forming units and a variety of different phosphine-containing amino acids have been examined for their ability to control the selectivity of the allylation reaction. This paper reports the results obtained through the examination of different turn motifs as well as different phosphine substitutions on the "best" turn sequence, Pps-Pro-D-Xxx-Pps.