118904-37-3

Basic information

• Product Name: FMOC-D-ALLO-ILE-OH
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-D-ALLO-ISOLEUCINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-ALLO-ISOLEUCINE;FMOC-D-ALLO-ILE-OH;FMOC-D-ALLO-ISOLEUCINE;D-N-FMOC-ALLOISOLEUCINE;(2R,3S)-N-FMOC-2-AMINO-3-METHYLPENTANOIC ACID;Fmoc-D-allo-lle-OH;N-ALPHA-(9-FLUOROENYLMETHYLOXYCARBONYL)-D-ALLO-ISOLEUCINE
• CAS NO: 118904-37-3
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.41
• Product Categories: Fmoc-Amino Acids and Derivatives
• Mol File: 118904-37-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 559.8 °C at 760 mmHg
• Flash Point: 292.4 °C
• Appearance: /Solid
• Density: 1.207 g/cm³
• Vapor Pressure: 2.28E-13mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: Store at RT.
• PKA: 3.92±0.22(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: FMOC-D-ALLO-ILE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-ALLO-ILE-OH(118904-37-3)
• EPA Substance Registry System: FMOC-D-ALLO-ILE-OH(118904-37-3)

Safety Data

• Hazardous Substances Data: 118904-37-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

Fmoc-D-Allo-Ile-OH is used in preparation of Cyclopeptides simulating natural product structures.

InChI:InChI=1/C21H23NO4/c1-3-13(2)19(20(23)24)22-21(25)26-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,13,18-19H,3,12H2,1-2H3,(H,22,25)(H,23,24)/t13-,19+/m0/s1

Upstream product

• 118878-65-2 N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine methyl ester 

Relevant articles and documents

Total Synthesis of the Didemnins; III. - Synthesis of Protected (2R,3S)-Alloisoleucine and (3S,4R,5S)-Isostatine Derivatives - Amino Acids from Hydroxy Acids

(2S,3S)-2-Acetoxy-3-methylvaleric acid (3) is prepared from L-isoleucine (2) with 96percent retention of configuration.Compound 3 is converted to optically pure methyl D-alloisoleucinate (7) as its hydrochloride salt, via the methanesulfonate 5 and the azide 6 with 76percent yield and 99.9percent inversion.Subsequent protection-saponification-activation of 7, followed by reaction with the lithium enolate of methyl trimethylsilyl malonate and reduction, yields (3S,4R,5S)-N-(9-fluorenylmethoxycarbonyl)isostatine (12). (3S,4R,5S)-Isostatine is a characteristic unit of the didemnines 1.