Protected amino alcohols are essential building blocks in modern drug discovery: they combine the stereochemical fidelity of amino acids with the flexible downstream chemistry of a primary alcohol. (R)-N-Fmoc-S-trityl cysteinol packages an Fmoc-protected amine, an S-trityl-protected thiol, and a terminal alcohol on a chiral cysteine-derived scaffold — a motif appearing in renin-inhibitor chemistry, peptidomimetics, and thioether/oxidation-sensitive constructs.
Chemical Identity and Key Properties
| Property | Value |
|---|---|
| CAS Number | 103213-32-7 |
| Molecular Formula | C37H33NO3S |
| Molecular Weight | 571.22 g/mol |
| Typical Purity | ≥98% (TLC), ≥98.0% (acidimetric), ≥99.0% (HPLC) |
Protecting-Group Strategy
The Fmoc group departs under mild base (piperidine/DMF), the acid-labile trityl sulfide survives repeated Fmoc cycles, and the primary alcohol is a handle for oxidation, sulfonate displacement, or ester/amide elaboration — three orthogonal handles on one chiral core.
Applications
Peptide and Peptidomimetic Synthesis
Solid-phase and solution incorporation of the cysteinol unit introduces a reduced-amide backbone isostere or a functionalized side-chain thiol after detritylation.
Medicinal Chemistry Scaffolds
The free thiol (post-deprotection) enables conjugation chemistry; the alcohol supports prodrug linkers and heterocycle formation.
Quality and Sourcing
Enantiomeric purity (chiral HPLC), Fmoc integrity, and trityl retention are the specification cornerstones; typical catalog purity is ≥98% by HPLC with TLC and acidimetric cross-assays. Store cold, dry, and protected from light.
Frequently Asked Questions
What enantiomeric excess is available?
Chiral synthesis and chiral-HPLC-verified material is available with ee specifications on request.
What are the standard purity assays?
HPLC purity with identity by NMR/MS; TLC and acidimetric assays are common supplementary data on the COA.
Can this building block be custom-made at scale?
Yes — CoreyChem manufactures protected amino alcohols and Fmoc derivatives from gram to kilogram scale with full analytical documentation.
Source from CoreyChem
CoreyChem supplies (R)-(9H-Fluoren-9-yl)methyl (1-hydroxy-3-(tritylthio)propan-2-yl)carbamate (CAS 103213-32-7) with lot-specific COA and MSDS documentation. Custom synthesis, higher purity grades, and bulk packaging are available on request — contact our technical team with your target specification and quantity for current lead time and pricing.
