284031-44-3

Basic information

• Product Name: 1H-Azepine-3,4,5-triol, hexahydro-, (3R,4S,5R)- (9CI)
• Synonyms: 1H-Azepine-3,4,5-triol, hexahydro-, (3R,4S,5R)- (9CI)
• CAS NO: 284031-44-3
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.17232
• Product Categories: ALCOHOL
• Mol File: 284031-44-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Azepine-3,4,5-triol, hexahydro-, (3R,4S,5R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Azepine-3,4,5-triol, hexahydro-, (3R,4S,5R)- (9CI)(284031-44-3)
• EPA Substance Registry System: 1H-Azepine-3,4,5-triol, hexahydro-, (3R,4S,5R)- (9CI)(284031-44-3)

Safety Data

• Hazardous Substances Data: 284031-44-3(Hazardous Substances Data)

Upstream product

• 943032-39-1 C₂₁H₃₁NO₆ 
• 114949-90-5 6-amino-2,6-dideoxy-D-arabino-hexono-1,6-lactam 
• 943032-38-0 (3R,4R,5R)-1-benzyl-3-O-acetyl-4,5-O-cyclohexylidene-3,4,5-trihydroxyazepane 
• 848837-65-0 C₁₄H₂₀O₄ 
• 848837-67-2 C₁₄H₂₂O₆ 
• 848837-64-9 C₁₄H₂₂O₆ 
• 609355-97-7 5,6-dideoxy-6-(N-benzyloxycarbonyl)amino-1,2-O-isopropylidene-α-D-gluco-furanose 
• 848862-10-2 (3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane 
• 848862-07-7 2,3-di-O-benzoyl-4,5-dideoxy-D-threo-pent-4-enose 
• 848862-09-9 (3R,4S,5S)-3,4-dibenzoyloxy-8-oxa-1-azabicyclo[3.2.1]octane 
• 609355-96-6 Benzyl-[2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-amine 
• 76801-66-6 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose 
• 745809-24-9 C₁₄H₂₀O₄ 

Relevant articles and documents

Concise and practical route to tri- and tetra-hydroxy seven-membered iminocyclitols as glycosidase inhibitors from d-(+)-glucurono-γ-lactone

An efficient and short total synthesis of tetrahydroxy-1c and trihydroxy-azepane 1d is reported in 72% and 57% overall yields, respectively, from d-(+)-glucurono-γ-lactone. Thus, d-glucuronolactone 2 on acetonide protection, DIBAL-H reduction and one-pot intermolecular reductive amination followed by -NCbz protection afforded 6-(N-benzyl-N-benzyloxycarbonyl) amino-6-deoxy-1,2-O-isopropylidene-α-d-gluco-1,4-furanose 5a. 1,2-Acetonide hydrolysis in 5a and Pd-mediated intramolecular reductive aminocyclization afforded tetrahydroxyazepane 1c. An analogous pathway with 5-deoxy-1,2-O-isopropylidene-α-d-glucurono-6,3-lactone 3b gave trihydroxy-azepane 1d. Glycosidase inhibitory activity of 1c/1d was studied and 1d was found to be potent inhibitor of α-mannosidase and β-galactosidase.

Expeditious synthesis of tri- and tetrahydroxyazepanes from D-(-)-quinic acid as potent glycosidase inhibitors

(Chemical Equation Presented) Several new stereoisomers of 3,4,6-trihydroxyazepanes and 7-hydroxymethyl-3,4,5-trihydroxyazepanes as well as known 3,4,5-trihydroxyazepanes were synthesized as potent glycosidase inhibitors from D-(-)-quinic acid in an effic

Synthesis of a trihydroxylated azepane from D-arabinose by way of an intramolecular alkene nitrone cycloaddition

The synthesis of 1,6-imino-1,5,6-trideoxy-l-xylo-hexitol, a trihydroxylated azepane, from d-arabinose was achieved by way of an intramolecular alkene nitrone cycloaddition. The final product as well as its bicyclic precursor, (3R,4S,5S)-3,4-dihydroxy-8-ox

An expeditious synthesis of a (3S,4S,5R)-trihydroxyazepane

A practical approach for the synthesis of the (2S,3S,4R)-trihydroxyazepane 1d has been reported. Starting from α-D-xylo-pentodialdose, readily available from D-glucose, the sequence involves Wittig olefination and reductive amination as key steps.

Chemo-enzymatic synthesis of polyhydroxyazepanes

Galactose oxidase (EC 1.1.3.9, GAO) is an extracellular copper-containing enzyme that utilizes molecular oxygen to convert the C6-primary hydroxyl moiety of D-galactopyranosides to hydrated aldehydes. Subsequent dehydratative coupling with hydroxylamines produces oximes (3a-f), which, when subjected to conditions of hydrogenolysis, give rise to polyhydroxyazepanes (11-17).

Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-1,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-ribo-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd.