178964-40-4

Usage

Uses

Used in Oncology:
(3R,4R,5R,6R)-3,4,5,6-TETRAHYDROXYAZEPANE HCL is used as a targeted therapy for the treatment of non-small cell lung cancer (NSCLC) that has specific EGFR mutations. It works by binding to the EGFR kinase domain, inhibiting the phosphorylation and activation of downstream signaling pathways, ultimately leading to the inhibition of cancer cell proliferation and survival. This makes it a valuable treatment option for patients with EGFR-mutant NSCLC who have developed resistance to other EGFR inhibitors.

Upstream product

• 71240-67-0 3,4-di-O-allyl-D-mannitol 
• 117371-06-9 benzyl 6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 157363-88-7 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-L-gulitol 
• 157363-85-4 1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol 
• 36199-02-7 3,4-di-O-benzyl-D-mannitol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 71223-75-1 3,4-di-O-allyl-1,2:5,6-dianhydro-D-mannitol 
• 58315-80-3 3,4-di-O-allyl-1,2:5,6-di-O-isopropylidene-D-mannitol 
• 280745-35-9 2,3:4,5-Di-O-isopropylidene-D-manno-hexodialdose 
• 280745-36-0 (3R,4R,5R,6R)-N-Benzhydryl-3,4:5,6-bis(isopropylidenedioxy)azepane 
• 488827-83-4 1,6-anhydro-N-(2,2-diethoxycarbonylvinyl)-β-D-mannopyranosylamine 
• 22435-75-2 N-(2,2-diethoxycarbonylvinyl)-β-D-mannopyranosylamine 
• 488827-86-7 1,6-anhydro-β-D-mannopyranosylamine 

Downstream Products

• 280783-58-6 (3R,4R,5R,6R)-3,4,5,6-Tetraacetoxy-N-acetylazepane 

Relevant academic research and scientific papers

Short practical synthesis of (3R,4R,5R,6A)-tetrahydroxyazepane and (3S,4S,5S,6S)-trahydroxyazepane from D- And L-chiroinositol, respectively

The polyhydroxylated azepanes (3R,4R,5R,6R)-tetrahydroxyazepane (-)-l and (35,45,5S,65)-tetrahydroxyazepane (+)-1 are synthesised from D-and L-c/j/ro-inositol, respectively. Key transformations in the reaction sequence include a glycol-fission reaction wi

An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines

A new stereocontrolled and high yielding synthesis of biologically active polyhydroxyperhydroazepines is reported starting from easily available glycosylenamines (D-gluco, D-manno, and D-galacto configurations), which are transformed into 1,6-azaanhydropy

Synthesis of azasugars as potent inhibitors of glycosidases

A series of enantiomerically pure azasugars (2,5-dideoxy-2,5-imino-D-mannitol, 1-deoxynojirimycin, 1-deoxymannojirimycin, and related compounds) was synthesized from D-mannitol via aminoheterocyclization of C2-symmetric bis-epoxides and subsequently followed by ring isomerization in few cases. These compounds have been evaluated as inhibitors of several glycosidases (α- and β-D-glucosidases, α-D-mannosidase and α-L-fucosidase). Inhibition studies indicate notably that the polyhydroxylated azepanes are inhibitors of glycosidases, with K(i) in the micromolar range.

Synthesis of C2-symmetrical polyhydroxyazepanes as inhibitors of glycosidases

Two C2-symmetrical bis-epoxides were prepared from D-mannitol and were subjected to nucleophilic displacements with allylamine and benzylamine. Initial intermolecular epoxide opening, followed by a preferred intramolecular 7-endo-tetragol cyclization, afforded protected polyhydroxyazepanes as major products. Compound 15 was found to inhibit seven different glycosidases with K(i) in the micromolar range.

C2-symmetrical tetrahydroxyazepanes as inhibitors of glycosidases and HIV/FIV proteases.

C2-Symmetrical tetrahydroxyazepanes were synthesized as inhibitors for glycosidases. Tetrahydroxyazepane 1 is a non-specific inhibitor of various glycosidases, while compounds 2, 3 and 4 specifically inhibit beta-N-acetylglucosaminidase, beta-glucosidase, and alpha-fucosidase, respectively, with Ki in the micromolar range. Compound 1 is not an inhibitor of HIV/FIV proteases, but its 3,6-difluorobenzyl derivatives are moderate inhibitors of both enzymes.

Enzymatic/chemical synthesis and biological evaluation of seven-membered iminocyclitols

Several polyhydroxyperhydroazepines have been obtained either by chemoenzymatic or chemical synthesis. Condensation of (±)-3-azido-2-hydroxypropanaldehyde and dihydroxyacetone phosphate (DHAP) in the presence of a DHAP dependent aldolase followed by treat

Polyhydroxylated Piperidines and Azepanes from D-Mannitol. Synthesis of 1-Deoxynojirimycin and Analogues

D-mannitol and L-iditol bis-epoxides, easily obtained from D-mannitol, are convenient substrates for the synthesis of polyhydroxylated piperidines and azepanes, via a nucleophilic opening of one epoxy function followed by a spontaneous intramolecular ring closure.Using this strategy 1-deoxynojirimycin and analogues were prepared. - Key words: D-mannitol, Piperidine, Azepane, 1-deoxynojirimycin, 1,5-dideoxy-1,5-imino-L-gulitol, β-Glycosidase inhibitor.