646068-80-6

Basic information

• Product Name: Butanoic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-[(triphenylmethyl)thio]-, (3R)-
• Synonyms: (R)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(triphenylmethyl)sulfanyl]butanoic acid;Fmoc-β3hCys(Trt)-OH;(R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-tritylsulfanyl-butyric acid;Fmoc-(R)-β3hCys(Tr)-OH
• CAS NO: 646068-80-6
• Molecular Formula: C38H33NO4S
• Molecular Weight: 599.75
• Mol File: 646068-80-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 88-90 °C
• Boiling Point: 780.1±60.0 °C(Predicted)
• Density: 1.256±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Butanoic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-[(triphenylmethyl)thio]-, (3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-[(triphenylmethyl)thio]-, (3R)-(646068-80-6)
• EPA Substance Registry System: Butanoic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-[(triphenylmethyl)thio]-, (3R)-(646068-80-6)

Safety Data

• Hazardous Substances Data: 646068-80-6(Hazardous Substances Data)

Usage

General Description

Butanoic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-[(triphenylmethyl)thio]-, (3R)- is a chemical compound with a complex structure. It contains a butanoic acid group, a carbonyl amino group attached to a fluoren-9-ylmethoxy group, and a triphenylmethylthio group. The compound is optically active, with a stereochemistry designated as (3R). Butanoic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-[(triphenylmethyl)thio]-, (3R)- may have potential applications in pharmaceuticals, organic synthesis, or materials science due to its unique structure and properties, but further research would be needed to determine its specific uses and effects.

Upstream product

• 76-83-5 trityl chloride 
• 712351-75-2 Fmoc-(R)-β³hCys-OH 
• 141892-41-3 Fmoc-L-Cys(PMB)-OH 
• 646068-79-3 3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(4-methoxy-benzylsulfanyl)-butyric acid 
• 847153-39-3 (R)-1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-{[(4-methoxy)benzyl]thio}butan-2-one 
• 646068-87-3 (R)-4-{[(acetamido)methyl]thio}-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid 
• 847153-40-6 (R)-4-{[(acetamido)methyl]thio}-1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butan-2-one 
• 86060-81-3 S-[(acetylamino)methyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine 

Relevant articles and documents

Preparation of protected β2- and β3- homocysteine, β2- and β3-homohistidine, and β2-homoserine for solid-phase syntheses

The Ser, Cys, and His side chains play decisive roles in the syntheses, structures, and functions of proteins and enzymes. For our structural and biomedical investigations of β-peptides consisting of amino acids with proteinogenic side chains, we needed to have reliable preparative access to the title compounds. The two β3-homoamino acid derivatives were obtained by Arndt-Eistert methodology from Boc-His(Ts)-OH and Fmoc-Cys(PMB)-OH (Schemes 2-4), with the side-chain functional groups' reactivities requiring special precautions. The β2-homoamino acids were prepared with the help of the chiral oxazolidinone auxiliary DIOZ by diastereoselective aldol additions of suitable Ti-enolates to formaldehyde (generated in situ from trioxane) and subsequent functional-group manipulations. These include OH → OtBu etherification (for β2hSer; Schemes 5 and 6), OH → STrt replacement (for β2hCys; Scheme 7), and CH 2OH → CH2N3 → CH2NH 2 transformations (for β2hHis; Schemes 9-11). Including protection/deprotection/re-protection reactions, it takes up to ten steps to obtain the enantiomerically pure target compounds from commercial precursors. Unsuccessful approaches, pitfalls, and optimization procedures are also discussed. The final products and the intermediate compounds are fully characterized by retention times (tR), melting points, optical rotations, HPLC on chiral columns, IR, 1H- and 13C-NMR spectroscopy, mass spectrometry, elemental analyses, and (in some cases) by X-ray crystal-structure analysis.