66224-56-4

Basic information

• Product Name: (3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL
• Synonyms: (3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL
• CAS NO: 66224-56-4
• Molecular Formula: C₇H₁₃N₃O₅
• Molecular Weight: 219.19522
• Mol File: 66224-56-4.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL(66224-56-4)
• EPA Substance Registry System: (3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL(66224-56-4)

Safety Data

• Hazardous Substances Data: 66224-56-4(Hazardous Substances Data)

Usage

Description

(3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL is a chiral chemical compound characterized by a tetrahydropyran ring structure, featuring an azidomethyl and a methoxy group. With a molecular formula of C8H15N3O4 and a molecular weight of 217.22 g/mol, this compound exhibits stereochemistry due to the presence of two asymmetric carbon centers, leading to four possible stereoisomers. Its unique structural features suggest potential applications in various fields such as organic synthesis, medicinal chemistry, and chemical biology.

Uses

Used in Organic Synthesis:
(3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL serves as a valuable intermediate in organic synthesis, particularly for the development of complex organic molecules and pharmaceutical agents. Its azide and methoxy functionalities can be strategically utilized in various synthetic transformations, making it a versatile building block for creating novel compounds with diverse applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL is employed as a key component in the design and synthesis of potential drug candidates. Its unique stereochemistry and functional groups can be exploited to create molecules with specific biological activities, targeting various therapeutic areas such as oncology, infectious diseases, and neurological disorders.
Used in Chemical Biology:
(3S,5S)-2-AZIDOMETHYL-6-METHOXY-TETRAHYDRO-PYRAN-3,4,5-TRIOL also finds application in chemical biology, where it can be used to probe and manipulate biological systems. Its azide group, in particular, can be employed in click chemistry approaches to label biomolecules or construct bioconjugates, enabling the study of biological processes and the development of new diagnostic and therapeutic tools.

Upstream product

• 51103-66-3 methyl 6-O-(p-tolylsulfonyl)-α-D-mannopyranoside 
• 20744-42-7 methyl 2,3-di-O-acetyl-6-azido-4-O-benzoyl-6-deoxy-α-D-mannopyranoside 
• 87586-20-7 2,4,6-Trimethyl-benzenesulfonic acid (2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 92528-09-1 methyl 6-azido-6-deoxy-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 18439-60-6 methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 18439-61-7 methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-mannopyranoside 
• 139978-81-7 methyl 2,3-O-isopropylidene-α-D-mannopyranoside 4,6-sulfite 
• 139978-82-8 methyl-2,3-O-isopropylidene-4,6-cyclic sulfate-α-D-mannopyranoside 
• 63167-69-1 methyl 2,3-O-isopropylidene-α-D-mannopyranoside 
• 4990-80-1 Methyl-6-chlor-6-deoxy-α-D-mannopyranosid 

Downstream Products

• 79695-15-1 methyl 6-amino-6-deoxy-α-D-mannopyrannoside 
• 138332-00-0 6-azido-6-deoxy-D-talose 
• 66224-57-5 methyl 6-azido-6-deoxy-2,3-di-O-benzylidene-α-D-mannopyranoside 
• 1270918-38-1 methyl 6-deoxy-6-N-[1,4]diazepane-1-carboxylic acid benzyl ester azepan-5-one-α-Dmannopyranoside 
• 1270918-35-8 methyl 6-deoxy-6-N-(5R)-phenyl-azepan-2-one-α-D-mannopyranoside 
• 1270918-36-9 methyl 6-deoxy-2,3,4-tri-O-acetyl-6-N-(5R)-phenyl-azepan-2-one-α-D-mannopyranoside. 
• 68396-86-1 methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside 
• 1326710-50-2 C₁₄H₁₅Cl₂NO₅ 
• 1354049-02-7 (3aS,4S,5aR,11aR,11bS)-8-(4-chlorophenyl)-4-methoxy-2,2-dimethyl-10-phenyl-3a,4,5a,6,11a,11b-hexahydro[1,3]dioxolo[4,5]pyrano[3,2-b][1,5]oxazocine 
• 1354049-03-8 (3aS,4S,5aR,11aR,11bS)-4-methoxy-2,2-dimethyl-10-phenyl-8-(2-thienyl)-3a,4,5a,6,11a,11b-hexahydro[1,3]dioxolo[4,5]pyrano[3,2-b][1,5]oxazocine 
• 1354049-05-0 (3aS,4S,5aR,11aR,11bS)-4-methoxy-2,2-dimethyl-8,10-diphenyl-3a,4,5a,6,11a,11b-hexahydro[1,3]dioxolo[4,5]pyrano[3,2-b][1,5]oxazocine 
• 1354049-06-1 (3aS,4S,5aR,11aR,11bS)-8-(3-flurophenyl)-4-methoxy-2,2-dimethyl-10-phenyl-3a,4,5a,6,11a,11b-hexahydro[1,3]dioxolo[4,5]pyrano[3,2-b][1,5]oxazocine 
• 1357280-97-7 (3R,4R,5R,6R)-3-hydroxy-4,5,6-tribenzyloxyazepane 
• 1357280-99-9 (3R,4R,5R,6R)-N-benzyloxycarbonyl-3-hydroxy-4,5,6-tribenzyloxyazepane 

Relevant articles and documents

New [(η5-C5H5)Ru(N-N)(PPh3)][PF6] compounds: Colon anticancer activity and GLUT-mediated cellular uptake of carbohydrate-appended complexes

Eight ruthenium(ii) compounds of the general formula [(η5-C5H5)Ru(N-N)(PPh3)][PF6] were rationally designed, exhibiting high cytotoxicity against HCT116 human colon cancer cells, with IC50

Gold nanoparticles decorated with mannose-6-phosphate analogues

Herein, the preparation of neoglycoconjugates bearing mannose-6-phosphate analogues is described by: (a) synthesis of a cyclic sulfate precursor to access the carbohydrate head-group by nucleophilic displacement with an appropriate nucleophile; (b) introduction of spacers on the mannose-6-phosphate analogues via Huisgen's cycloaddition, the Julia reaction, or the thiol-ene reaction under ultrasound activation. With the resulting compounds in hand, gold nanoparticles could be functionalized with various carbohydrate derivatives (glycoconjugates) and then tested for angiogenic activity. It was observed that the length and flexibility of the spacer separating the sugar analogue from the nanoparticle have little influence on the biological response. One particular nanoparticle system substantially inhibits blood vessel growth in contrast to activation by the corresponding monomeric glycoconjugate, thereby demonstrating the importance of multivalency in angiogenic activity.