215190-17-3

Basic information

• Product Name: FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID
• Synonyms: FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID;FMOC-AHMHPA;FMOC-AHMHPA-OH;FMOC-(S,S,S)AHMHPA-OH;(3S,4S,5S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-3-hydroxy-5-methylheptanoic acid;Fmoc-(3S,4S,5S)-4-amino-3-hydroxy-5-methylheptanoic acid≥ 98% (HPLC);Fmoc-AHMHpA(3S,4S,5S)-OH
• CAS NO: 215190-17-3
• Molecular Formula: C23H27NO5
• Molecular Weight: 397.46
• Mol File: 215190-17-3.mol

Chemical Properties

• Boiling Point: 628.2±55.0 °C(Predicted)
• Appearance: /
• Density: 1.228±0.06 g/cm3(Predicted)
• Storage Temp.: Store at 0°C
• PKA: 4.23±0.10(Predicted)
• CAS DataBase Reference: FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID(215190-17-3)
• EPA Substance Registry System: FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID(215190-17-3)

Safety Data

• Hazardous Substances Data: 215190-17-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its unique structure and stereochemistry allow for the creation of complex molecules with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID is used as a building block for the synthesis of various organic compounds. Its versatility and specific stereochemistry make it a valuable tool for researchers in designing and creating novel molecules with desired properties.
Used in Peptide Synthesis:
FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID is used as a key component in the synthesis of peptides. Its incorporation into peptide sequences can lead to the development of new bioactive peptides with potential applications in medicine and biotechnology.
Used in Drug Delivery Systems:
FMOC-(3S,4S, 5S)-4-AMINO-3-HYDROXY-5-METHYL HEPTANOIC ACID can be utilized in the development of drug delivery systems, where its unique properties can be harnessed to improve the targeting, release, and overall efficacy of therapeutic agents.

Upstream product

• 118878-56-1 Methyl (4S,5S)-4-(9-fluorenylmethoxycarbonylamino)-5-methyl-3-oxoheptanoate 
• 118878-65-2 N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine methyl ester 
• 118904-37-3 N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine 
• 118878-54-9 (4S,5S)-4-(9-Fluorenylmethoxycarbonylamino)-5-methyl-3-oxoheptanoyl chloride 
• 118878-57-2 (3S,4R,5S)-N-(9-Fluorenylmethoxycarbonyl)isostatine methyl ester 
• 129867-96-5 tert-butyl (3S,4R,5S)-4-(9-fluorenylmethoxycarbonylamino)-3-hydroxy-5-methylheptanoate 

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.

TOTAL SYNTHESIS OF THE DIDEMNINS - 1. SYNTHESIS OF THE PEPTOLIDE RING

The 23-membered peptolide ring of the didemnins is formed in a two phase cyclization of a linear ω-amino-pentafluorophenyl ester in 70percent yield without high dilution. (2RS,4S)-2,5-dimethyl-4-hydroxy-3-oxohexanoic acid (Hip) and (3S,4R,5S)-isostatine are synthesized by acylations of trimethylsilyl malonates.