132684-60-7

Basic information

• Product Name: Fmoc-L-tert-leucine
• Synonyms: FMOC-L-TLE-OH;FMOC-L-T-BUTYLGLYCINE;FMOC-L-TERT-LEUCINE;FMOC-TLE-OH;FMOC-TBU-GLYCINE;FMOC-TBU-GLY-OH;FMOC-ALPHA-T-BUTYL-GLY-OH;FMOC-ALPHA-T-BUTYLGLYCINE
• CAS NO: 132684-60-7
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.41
• Product Categories: API intermediates;Amino Acids;Amino Acids & Deriv.;CHIRAL CHEMICALS;Peptide
• Mol File: 132684-60-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 124-127 °C
• Boiling Point: 554.1 °C at 760 mmHg
• Flash Point: 288.9 °C
• Appearance: /
• Density: 1.209 g/cm³
• Vapor Pressure: 4.12E-13mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 2-8°C
• PKA: 3.92±0.10(Predicted)
• BRN: 6662856
• CAS DataBase Reference: Fmoc-L-tert-leucine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-tert-leucine(132684-60-7)
• EPA Substance Registry System: Fmoc-L-tert-leucine(132684-60-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 132684-60-7(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

Fmoc-Tle-OH is a versatile reactant used in the discovery of potent antagonists of antiapoptotic protein X-linked inhibitor of apoptosis (XIAP) for treatment of cancer. It is also used as reactant in the preparation of phosphino dipeptide derivatices as ligand in copper-phosphine catalyst for asymmetric conjugate addition of alkylzinc reagents to unsaturated ketones.

InChI:InChI=1/C21H23NO4/c1-21(2,3)18(19(23)24)22-20(25)26-12-17-15-10-6-4-8-13(15)14-9-5-7-11-16(14)17/h4-11,17-18H,12H2,1-3H3,(H,22,25)(H,23,24)/t18-/m1/s1

Upstream product

• 20859-02-3 L-tert-Leucine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 24324-17-2 9-Fluorenylmethanol 
• 139163-43-2 (S)-2-amino-3,3-dimethylbutanoic acid hydrochloride 
• 471-50-1 2-L-amino-3,3-dimethylbutyric acid 

Downstream Products

• 1067650-16-1 C₃₆H₄₄N₂O₅ 
• 1231171-63-3 DOTA-NLys⁽⁸⁾-Lys⁽⁹⁾-Pro⁽¹⁰⁾-Tyr⁽¹¹⁾-Tle⁽¹²⁾-Leu⁽¹³⁾ 

Relevant articles and documents

ATAZANAVIR (ATV) ANALOGUES FOR TREATING HIV INFECTIONS

The invention provides a compound of Formula I: or a pharmaceutically acceptable salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of Formula I, processes for preparing compounds of Formula I, the compound of formula (I) for use in therapeutic methods for treating the proliferation of the HIV virus, treating AIDS or delaying the onset of AIDS symptoms in a mammal using compounds of Formula I. Preferred compounds are N-[(2S) -1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino) -3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(phenyl) methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate atazanavir (ATV) analogues substituted by several heterocycles, such as e.g. pyrazole (Rl); e.g. oxetane (substituent of X2); e.g. pyridine or pyrimidine (X1); e.g. piperazine or 3,8-diazabicyclo[3.2.1]octan (X2).

Ureidopeptide-based Bronsted bases: Design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles

The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Bronsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis. Learning from peptides: A concise route for the catalytic enantioselective synthesis of β-amino nitriles has been achieved by using ureidopeptide-based Bronsted bases as catalysts in the Mannich reaction of N-Boc imines and (arylsulfonyl)acetonitriles (see scheme; Boc=tert-butoxycarbonyl, napht=naphthyl, TMS=trimethylsilyl).

Catalytic asymmetric acylcyanation of imines

(Chemical Equation Presented) The less problematic acetyl cyanide can be used instead of toxic HCN for the highly enantioselective acyl-Strecker-type reaction. In the presence of an N-benzylimine and a catalytic amount of Jacobsen's catalyst 1, the desire