190656-01-0

Usage

Uses

Used in Organic Chemistry:
9-FLUORENYLMETHYL N-HYDROXYCARBAMATE is used as a reactant for the synthesis of [N-Fmoc-aminooxy-2-chlorotrityl polystyrene] because it serves as a solid-phase resin in the production of hydroxamic acids and peptidyl hydroxamic acids, which are essential in various chemical and pharmaceutical applications.
Used in Pharmaceutical Industry:
9-FLUORENYLMETHYL N-HYDROXYCARBAMATE is used as a reactant for the synthesis of [9-Fluorenylmethyl nosyloxycarbamate (Fmoc-NHONs)] for [reacting with nosyl chloride], which is an important step in the development of new pharmaceutical compounds and drug candidates.

InChI:InChI=1/C15H13NO3/c17-15(16-18)19-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14,18H,9H2,(H,16,17)

Upstream product

• 144-55-8 sodium hydrogencarbonate 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Downstream Products

• 729579-11-7 9-fluorenylmethyl nosyloxycarbamate 
• 1352786-35-6 (9H-fluoren-9-yl)methyl benzoyloxycarbamate 
• 1391993-19-3 N-Fmoc-hydroxyamine O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 1391993-20-6 N-Fmoc-hydroxyamine O-2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 1391993-21-7 N-Fmoc-hydroxyamine O-2,3,4-tri-O-benzoyl-6-deoxy-α-L-rhamnopyranoside 
• 1391993-22-8 N-Fmoc-hydroxyamine O-2,3,4-tri-O-benzoyl-6-deoxy-α-L-talopyranoside 
• 1440756-26-2 (9H-fluoren-9-yl)methyl (2,4,6-trichlorobenzoyl)oxycarbamate 
• 1440754-18-6 (9H-fluoren-9-yl)methyl (2-(pyridin-2-yl)phenyl)carbamate 
• 683217-51-8 (±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-cyclopropylpropanoic acid 
• 180181-93-5 (±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid 
• 282524-78-1 (±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-phenylbutanoic acid 

Relevant academic research and scientific papers

N-Fmoc-aminooxy-2-chlorotrityl polystyrene resin: A facile solid-phase methodology for the synthesis of hydroxamic acids

Using the new compound N-Fmoc-hydroxylamine 1 we have generated a facile route to a high loading, acid labile solid-phase resin bearing a hydroxylamine linker. The novel N-Fmoc-aminooxy-2-chlorotrityl polystyrene 2 showed generic utility for the construct

Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant

We previously reported that caffeoyl-amino acidyl-hydroxamic acid (CA-Xaa-NHOH) acted as both a good antioxidant and tyrosinase inhibitor, in particular when caffeic acid was conjugated with proline or amino acids having aromatic ring like phenylalanine. Here, various hydroxycinnamic acid (HCA) derivatives were further conjugated with phenylalanyl hydroxamic acid and prolyl hydroxamic acid (HCA-Phe-NHOH and HCA-Pro-NHOH) to study the structure and activity relationship as both antioxidants and tyrosinase inhibitors. When their biological activities were evaluated, all HCA-Phe-NHOH and HCA-Pro-NHOH exhibited enhanced antioxidant activity compared to HCA alone. Moreover, derivatives of caffeic acid, ferulic acid, and sinapic acid inhibited lipid peroxidation more efficiently than vitamin E analogue (Trolox). In addition, derivatives of caffeic acid and sinapic acid efficiently inhibited tyrosinase activity and reduced melanin content in melanocytes Mel-Ab cell.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

Mild and efficient Lewis acid-promoted detritylation in the synthesis of N-hydroxy amides: A concise synthesis of (-)-cobactin T

(Chemical Equation Presented) An efficient, high-yielding Lewis acid promoted deprotection of O-trityl hydroxylamine derivatives is described. A range of acid-labile protecting groups, such as N-Boc and O-TBS, were tolerated under these mild conditions. The present method is applicable to the synthesis of a broad range of hydroxylamine derivatives, including N-hydroxy amides (hydroxamic acids), N-hydroxy sulfonamides, and N-hydroxy ureas, which often exhibit significant biological activities. An application of this methodology for a concise synthesis of (-)-Cobactin T (18) is also demonstrated.

Collections of compounds

A compound of formula (IV): O is a solid support; L is a linking group or a single bond; X′ is selected from CO, NH, S, or O; A is O, S, NH, or a single bond; R2and R3are independently selected from: H, R, OH, OR, ═O, ═CH—R, ═CH2, CH2—CO2R′, CH2—CO2H, CH2—SO2R, O—SO2R, CO2R, COR, CN and there is optionally a double bond between C1 and C2 or C2 and C3; R6, R7, and R9are independently selected from H, R, OH, OR, halo, nitro, amino, Me3Sn; R11is either H or R; Q is S, O or NH; R10is a nitrogen protecting group; and Y is a divalent group such that HY=R, and other related compounds and collections of compounds.