148625-77-8

Basic information

• Product Name: FMOC-PRO-OL
• Synonyms: (S)-1-FMOC-2-PYRROLIDINEMETHANOL;(S)-N-FMOC-2-PYRROLIDINEMETHANOL;N-(9-FLUORENYLMETHOXYCARBONYL)-L-PROLINOL;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-PROLINOL;N-ALPHA-FMOC-L-PROLINOL;N-FMOC-L-PROLINOL;FMOC-L-PROLINOL;FMOC-L-PRO-OL
• CAS NO: 148625-77-8
• Molecular Formula: C₂₀H₂₁NO₃
• Molecular Weight: 323.39
• Product Categories: Amino Acids
• Mol File: 148625-77-8.mol

Chemical Properties

• Melting Point: 90℃
• Boiling Point: 504.638 °C at 760 mmHg
• Flash Point: 258.996 °C
• Appearance: /
• Density: 1.242 g/cm³
• Vapor Pressure: 5.26E-11mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: −20°C
• PKA: 14.77±0.10(Predicted)
• BRN: 8789847
• CAS DataBase Reference: FMOC-PRO-OL(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-PRO-OL(148625-77-8)
• EPA Substance Registry System: FMOC-PRO-OL(148625-77-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 148625-77-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
FMOC-PRO-OL is used as a synthetic intermediate for the development of various organic compounds. Its application in organic synthesis is due to its ability to facilitate the formation of complex molecular structures, which can be utilized in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, FMOC-PRO-OL is used as a building block for the synthesis of peptides and other bioactive molecules. Its role in this industry is to provide a versatile and efficient means of constructing peptide-based drugs, which can be employed for the treatment of various diseases and medical conditions.
Used in Research and Development:
FMOC-PRO-OL is also utilized in research and development settings, where it serves as a key component in the design and synthesis of novel compounds with potential applications in various fields, including medicine, agriculture, and materials science. Its use in R&D is driven by the need for innovative and effective solutions to address contemporary challenges in these areas.

InChI:InChI=1/C20H21NO3/c22-12-14-6-5-11-21(14)20(23)24-13-19-17-9-3-1-7-15(17)16-8-2-4-10-18(16)19/h1-4,7-10,14,19,22H,5-6,11-13H2/t14-/m0/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 186202-18-6 (S)-(-)-2,2,2-trifluoro-1-(2-(hydroxymethyl)pyrrolidin-1-yl)ethanone 
• 329309-00-4 Fmoc-Pro-N₃ 
• 71989-31-6 Fmoc-Pro-OH 

Downstream Products

• 929120-62-7 (R,E)-1-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3-((4-methoxyphenyl)dimethylsilyl)hex-4-en-1-one 
• 391624-45-6 2-[(4-nitro-phenoxycarbonylamino)-methyl]-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 886990-66-5 C₃₉H₅₂N₂O₅SSi 
• 886990-77-8 C₂₉H₅₀N₂O₃SSi 

Relevant articles and documents

O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups

Amino groups are selectively protected in good yields by reaction with O-Alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.

Asymmetric Michael addition reaction organocatalyzed by stereoisomeric pyrrolidine sulfinamides under neat conditions. A brief study of self-disproportionation of enantiomers

This paper describes the synthesis of all four possible stereoisomers of the pyrrolidine sulfinamides derived from (S)-proline or (R)-proline and either enantiomer of t-butylsulfinamide. These bifunctional derivatives were examined as organocatalysts in t

Single-stranded nucleic acid molecule having nitrogen-containing alicyclic skeleton

Provided is a novel nucleic acid molecule that can be produced easily and efficiently and can inhibit the expression of a gene. The nucleic acid molecule is a single-stranded nucleic acid molecule including an expression inhibitory sequence that inhibits expression of a target gene. The single-stranded nucleic acid molecule includes: a region (X); a linker region (Lx); and a region (Xc). The linker region (Lx) is linked between the regions (Xc) and (Xc). The region (Xc) is complementary to the region (X). At least one of the regions (X) and (Xc) includes the expression inhibitory sequence. The linker region (Lx) has a non-nucleotide structure including at least one of a pyrrolidine skeleton and a piperidine skeleton. According to this single-stranded nucleic acid molecule, it is possible to inhibit the expression of the target gene.

SINGLE-STRANDED NUCLEIC ACID MOLECULE FOR CONTROLLING GENE EXPRESSION

Provided is a novel nucleic acid molecule that can inhibit the expression of a gene and can be produces easily and efficiently. The nucleic acid molecule is a single-stranded nucleic acid molecule including an expression inhibitory sequence that inhibits expression of a target gene. The single-stranded nucleic acid molecule includes, in sequence from the 5′ side to the 3′ side: a 5′ side region (Xc); an inner region (Z); and a 3′ side region (Yc). The inner region (Z) is composed of an inner 5′ side region (X) and an inner 3′ side region (Y) that are linked to each other. The 5′ side region (Xc) is complementary to the inner 5′ side region (X). The 3′ side region (Yc) is complementary to the inner 3′ side region (Y). At least one of the inner region (Z), the 5′ side region (Xc), and the 3′ side region (Yc) includes the expression inhibitory sequence. According to this single-stranded nucleic acid molecule, it is possible to inhibit the expression of the target gene.

MULTICYCLIC COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are multicyclic compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

Simple and efficient synthesis of Fmoc/Boc/Cbz-protected-β-amino alcohols and peptidyl alcohols employing Boc2O

An efficient method for the activation of Fmoc/Boc/Cbz-protected amino acids using Boc2O and the reduction of the in situ generated carbonic-carbonic anhydride to their corresponding 1β-amino alcohols using sodium borohydride has been described. The method is simple, rapid and free from racemization. Besides, the protocol is also extended for the conversion of N-urethane protected peptide acids to their corresponding alcohols. Copyright

A simple synthesis of N β-Fmoc/Z-amino alkyl thiols and their use in the synthesis of N β-Fmoc/Z-amino alkyl sulfonic acids

A simple and efficient protocol for the synthesis of Nβ- Fmoc/Z-amino alkyl thiols is described. The approach uses sodium pyrosulfite-mediated hydrolysis of isothiouronium salts resulting from the reaction between N-protected aminoalkyl iodides and thiourea. N-Protected taurines were prepared through performic acid oxidation of the thiols and the products were further utilized for the synthesis of dipeptidosulfonamides. Georg Thieme Verlag Stuttgart - New York.

Using peptidyl aldehydes in activity-based proteomics

The broad inhibitory spectrum of aldehydes and the possibility that amino acid residues modulate their specificity point to the potential of using peptidyl aldehydes as activity-based probes. Here, we establish the potential of peptidyl aldehydes in activity-based proteomics by synthesizing different probes and using them to specifically label a well-known serine protease in an activity-dependent manner. From our results, peptidyl aldehydes emerge as promising activity-based probes that enable multiple enzymatic-class detection by substrate recognition and can be used in diverse activity-based proteomics applications like protein identification and activity profiling.

N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides

(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.

Asymmetric synthesis of highly substituted azapolycyclic compounds via 2-alkenyl sulfoximines: Potential scaffolds for peptide mimetics

The application of metalated, enantiomerically pure acyclic and cyclic 2-alkenyl sulfoximines for the synthesis of highly substituted aza(poly)cyclic ring systems is described. The method relies on a one-pot combination of a reagent-controlled allyl transfer reaction to α- or β-amino aldehydes, followed by a Michael-type cyclization of the intermediate vinyl sulfoximines generated in the first step. The sulfur-free target compounds are preferentially obtained by samarium iodide treatment of the sulfonimidoyl substituted heterocycles. In addition to this methodological work, initial results on the biological activity of selected examples are reported. Furthermore, a concept for the transformation of peptidic lead structures into non-peptide mimetics is described, and the relevance of the new approach to highly substituted azaheterocycles in this context is discussed.