170643-02-4

Basic information

• Product Name: FMOC-D-ALLO-THR(TBU)-OH
• Synonyms: FMOC-D-ALLO-THR(TBU)-OH;FMOC-D-ALLO-THREONINE(TBU)-OH;N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-O-T-BUTYL-D-ALLO-THREONINE;O-(tert-Butyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-allothreonine;FMOC-D-All-Thr(tBu)-OH;(2R,3R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-(tert-butoxy)butanoic acid;N-Fmoc-O-tert-butyl-D-allo-threonine;(9H-Fluoren-9-yl)MethOxy]Carbonyl D-Allo-Thr(tBu)-OH
• CAS NO: 170643-02-4
• Molecular Formula: C₂₃H₂₇NO₅
• Molecular Weight: 397.46
• Mol File: 170643-02-4.mol

Chemical Properties

• Boiling Point: 581.7±50.0 °C(Predicted)
• Appearance: White/Powder
• Density: 1.197
• PKA: 3.42±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-ALLO-THR(TBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-ALLO-THR(TBU)-OH(170643-02-4)
• EPA Substance Registry System: FMOC-D-ALLO-THR(TBU)-OH(170643-02-4)

Safety Data

• Hazardous Substances Data: 170643-02-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
FMOC-D-ALLO-THR(TBU)-OH is used as a key component in the synthesis of peptides for the development of pharmaceuticals. Its incorporation allows for the design of peptides with specific therapeutic properties, tailored to address various medical conditions.
Used in Biochemical Research:
In the realm of biochemical research, FMOC-D-ALLO-THR(TBU)-OH is employed as a tool to study the structure and function of proteins and enzymes. Its ability to form unique peptide sequences aids in understanding the intricate mechanisms of biological systems.
Used in Peptide Synthesis:
FMOC-D-ALLO-THR(TBU)-OH is used as a building block for peptide synthesis, providing a means to construct peptides with precise amino acid sequences. This capability is crucial for creating bioactive molecules with potential applications in medicine and biotechnology.
Used in Organic Chemistry:
FMOC-D-ALLO-THR(TBU)-OH is utilized in organic chemistry as a reagent for the synthesis of complex organic molecules. Its structural features facilitate the formation of specific chemical bonds and the development of novel compounds with potential applications across various industries.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 119323-52-3 (2R,3R)-2-Amino-3-tert-butoxy-butyric acid 
• 130674-54-3 (2R,3R)-2-N-(9-fluorenylmethyloxycarbonyl)-D-allothreonine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 1445907-66-3 C₃₂H₅₀N₆O₉S 
• 1310050-75-9 nobilamide B 
• 130674-54-3 (2R,3R)-2-N-(9-fluorenylmethyloxycarbonyl)-D-allothreonine 

Relevant articles and documents

Asymmetric synthesis of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives proper for solid-phase peptide coupling

Practical new routes for preparation of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives, the key structural components of cytotoxic marine peptides callipeltin O and Q, suitable for the Fmoc-SPPS, were developed. (2S,3S)-Fmoc-3-Me-Gln(Xan)-OH was synthesized via Michael addition reactions of Ni (II) complex of chiral Gly-Schiff base; while Fmoc-(R)-allo-Thr-OH was prepared using chiral Ni (II) complex-assisted α-epimerization methodology, starting form (S)-Thr(tBu)-OH.

Improved synthesis of d-allothreonine derivatives from l-threonine

The improved synthesis of protected d-allothreonine derivatives [Fmoc-d-alloThr(tBu)-OH (1) and Fmoc-d-alloThr-OtBu (2)] is described. The epimerization of cheap l-threonine (l-Thr) (3) with catalytic salicylaldehyde afforded a mixture of l-Thr (3) and d-alloThr (4) and separation of ammonium salt gave d-alloThr (4) in 96% de. The chemoselective deprotection of tert-butyl ether or tert-butyl ester of Fmoc-d-alloThr(tBu)-O tBu (5) easily succeeded in converting Fmoc-d-alloThr( tBu)-OH (1) or Fmoc-d-alloThr-OtBu (2), respectively.

Total synthesis of the large non-ribosomal peptide polytheonamide B

Polytheonamide B is by far the largest non-ribosomal peptide known at present, and displays extraordinary cytotoxicity (EC50 =68 pg ml -1 , mouse leukaemia P388 cells). Its 48 amino-acid residues include a variety of non-proteinogenic d- and l-amino acids, and the absolute stereochemistry of these amino acids alternate in sequence. These structural features induce the formation of a stable β-strand-type structure, giving rise to an overall tubular structure over 30A? in length. In a biological setting, this fold is believed to transport cations across the lipid bilayer through a pore, thereby acting as an ion channel. Here, we report the first chemical construction of polytheonamide B. Our synthesis relies on the combination of four key stages: syntheses of non-proteinogenic amino acids, a solid-phase assembly of four fragments of polytheonamide B, silver-mediated connection of the fragments and, finally, global deprotection. The synthetic material now available will allow studies of the relationships between its conformational properties, channel functions and cytotoxicity.

Synthesis of Nα-(9-Fluorenylmethoxycarbonyl)-Allothreonine t-Butyl Ether via Threonine Oxazolines

New procedures for the preparation of allothreonine, suitably protected for solid phase peptide synthesis, were developed.Stereochemical inversion in the side chain of threonine via thionyl chloride-induced oxazoline cyclisation and subsequent hydrolysis, followed by protection of the allothreonine amino and hydroxyl functions provided Fmoc-D-alloThr(But)-OH from benzoyl-D-threonine phenacyl ester in only five steps.Alternatively, it was shown that temporary carboxyl protection for introduction of the t-butyl ether group can be circumvented by direct selective ester acidolysis from Fmoc-Thr(But)-OBut.