176380-53-3

Basic information

• Product Name: N-Fmoc-L-threonol
• Synonyms: N-(9-FLUORENYLMETHOXYCARBONYL)-THREONINOL;N-FMOC-L-THREONINOL;9-FLUORENYLMETHYLOXYCARBONYL-L-THREONINOL;FMOC-(2R,3R)-2-AMINO-3-HYDROXY-1-BUTANOL;FMOC-THREONINOL;FMOC-THR-OL;FMOC-L-THREONINOL;FMOC-L-THR-OL
• CAS NO: 176380-53-3
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.37
• Product Categories: Threonine [Thr, T];Amino Alcohols;Fmoc-Amino acid series
• Mol File: 176380-53-3.mol

Chemical Properties

• Boiling Point: 586.5 °C at 760 mmHg
• Flash Point: 308.5 °C
• Appearance: /Solid
• Density: 1.259 g/cm³
• Vapor Pressure: 1.35E-14mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: -15°C
• PKA: 11.27±0.46(Predicted)
• CAS DataBase Reference: N-Fmoc-L-threonol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Fmoc-L-threonol(176380-53-3)
• EPA Substance Registry System: N-Fmoc-L-threonol(176380-53-3)

Safety Data

• Hazardous Substances Data: 176380-53-3(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry and Pharmaceutical Research:
N-Fmoc-L-threonol is utilized as a key component in peptide synthesis for the creation of peptides with specific sequences and properties. The Fmoc protecting group allows for the selective and controlled reactions necessary to produce peptides with desired characteristics, making it an indispensable tool in both academic and industrial research settings.
Used in Laboratory Settings:
In laboratories, N-Fmoc-L-threonol is employed as a building block for the synthesis of peptides. Its role is crucial in the development of peptides with tailored properties for various applications, including therapeutics, diagnostics, and research tools. The Fmoc group's protective function ensures that the hydroxyl group remains intact and unreacted until specifically targeted during the synthesis process, thus facilitating the production of peptides with high purity and specificity.

InChI:InChI=1/C19H21NO4/c1-12(22)18(10-21)20-19(23)24-11-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,12,17-18,21-22H,10-11H2,1H3,(H,20,23)/t12-,18-/m1/s1

Upstream product

• 377082-52-5 (2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-1-O-(tert-butyldimethylsilyl)butane-1,3-diol 
• 73731-37-0 Fmoc-Thr-OH 

Downstream Products

• 205109-16-6 N-fluorenyl-9-ylmethoxycarbonyl-L-threoninol p-carboxybenzacetal 
• 73731-37-0 Fmoc-Thr-OH 

Relevant articles and documents

Direct solid-phase synthesis of octreotide conjugates: Precursors for use as tumor-targeted radiopharmaceuticals

Somatostatin analogues, such as octreotide, are useful for the visualization and treatment of tumors. Unfortunately, these compounds were produced synthetically using complex and inefficient procedures. Here, we describe a novel approach for the synthesis of octreotide and its analogues using p-carboxybenzaldehyde to anchor Fmoc-threoninol to solid phase resins. The reaction of the two hydroxyl groups of Fmoc-threoninol with p-carboxybenzaldehyde was catalyzed with p-toluenesulphonic acid in chloroform using a Dean-Stark apparatus to form Fmoc-threoninol p-carboxybenzacetal in 91% yield. The Fmoc-threoninol p-carboxybenzacetal acted as an Fmoc-amino acid derivative and the carboxyl group of Fmoc-threoninol p-carboxybenzacetal was coupled to an amine-resin via a DCC coupling reaction. The synthesis of protected octreotide and its conjugates were carried out in their entirety using a conventional Fmoc protocol and an autosynthesizer. The acetal was stable during the stepwise elongation of each Fmoc-amino acid as shown by the averaged coupling yield (>95%). Octreotide (74 to 78% yield) and five conjugated derivatives were synthesized with high yields using this procedure, including three radiotherapy octreotides (62 to 75% yield) and two cellular markers (72 to 76% yield). This novel approach provides a strategy for the rapid and efficient large-scale synthesis of octreotide and its analogues for radiopharmaceutical and tagged conjugates.