Name & Type

Fmoc-threoninol p-carboxybenzacetal

in Pharmaceutical Intermediates, Type: sell

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  • Fmoc-threoninol p-carboxybenzacetal
  • HONG KONG PE BIOSCIENCES LIMITED is a manufacturer and exporter of highly qualified amino acids derivatives, peptides, proteins and enabling technologies for scientific research. Our comprehensive products consist […]

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 Country Of Origin: China
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Description

Product name: Fmoc-threoninol p-carboxybenzacetal

Synonym: 4-((4R,5R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methyl-1,3-dioxan-2-yl)benzoic acid,

Catalog #: 8132092

Purity: 95% by HPLC

CAS No.:

Molecular Formula: C27H25NO6

Molecular Weight: 459.50

Compound ID:

Description: 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.

 

Usage: For Scientific Research Use Only, Not for Human Use.

 

Reference:

Bioorg Med Chem. 1999 Sep;7(9):1797-803.

 

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