130674-54-3

Basic information

• Product Name: FMOC-D-ALLO-THR-OH
• Synonyms: FMOC-D-THR(ALLO)-OH;FMOC-D-ALLO-THR-OH;FMOC-D-ALLO-THREONINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-ALLO-THREONINE;N-alpha-(9-Fluorenylmethyloxycarbonyl)-allo-D-threonine;Fmoc-D-allo-threonine99%;(9H-Fluoren-9-yl)MethOxy]Carbonyl D-Allo-Thr-OH
• CAS NO: 130674-54-3
• Molecular Formula: C₁₉H₁₉NO₅
• Molecular Weight: 341.36
• Product Categories: Amino Acids
• Mol File: 130674-54-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 596.5 °C at 760 mmHg
• Flash Point: 314.6 °C
• Appearance: /
• Density: 1.327g/cm³
• Storage Temp.: Store at RT.
• PKA: 3.49±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-ALLO-THR-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-ALLO-THR-OH(130674-54-3)
• EPA Substance Registry System: FMOC-D-ALLO-THR-OH(130674-54-3)

Safety Data

• Hazardous Substances Data: 130674-54-3(Hazardous Substances Data)

Usage

General Description

FMOC-D-ALLO-THR-OH is a chemical compound that is classified as a derivative of the natural amino acid threonine. It contains a FMOC (9-fluorenylmethoxycarbonyl) protecting group, which is commonly used in peptide synthesis to protect the N-terminus of amino acids. The "D" in its name indicates that it is the D-stereoisomer of threonine, which is the mirror image of the naturally occurring L-stereoisomer. The "ALLO" in its name indicates that it is an allo-threonine derivative, which means that the hydroxyl group on the threonine side chain is in a different position than in the standard threonine molecule. FMOC-D-ALLO-THR-OH is often used in chemical synthesis and biochemistry research for the creation of peptides and proteins.

Upstream product

• 24830-94-2 D-allo-threonine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 170643-02-4 N^α-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether 

Downstream Products

• 868546-94-5 C₅₃H₈₅N₉O₁₄ 
• 913263-73-7 C₃₈H₆₀N₆O₁₀ 
• 1026305-60-1 C₄₄H₇₁N₇O₁₁ 
• 868546-95-6 C₅₃H₈₃N₉O₁₃ 
• 868546-92-3 C₄₉H₇₉N₉O₁₁ 
• 170643-02-4 N^α-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether 
• 1608124-50-0 C₆₆H₁₀₇N₁₅O₂₂ 
• 1608124-49-7 C₆₆H₁₀₇N₁₅O₂₂ 
• 1608124-47-5 C₆₆H₁₀₇N₁₅O₂₂ 
• 1608124-48-6 C₆₆H₁₀₇N₁₅O₂₂ 
• 72-19-5 L-threonine 
• 2812-27-3 N-methyl threonine 
• 2812-36-4 N,N-dimethyl-threonine 

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.

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.