127414-85-1

Basic information

• Product Name: calystegine B(2)
• Synonyms: calystegine B(2);Nortropanoline;(1R,2S,3R,4S,5R)-8-Azabicyclo[3.2.1]octane-1,2,3,4-tetrol;Calystegin B2;2-Epicalystegine B3;(1R,2S,3R,4S,5R)-8-azabicyclo[3.2.1]octane-2,3,4,5-tetrol
• CAS NO: 127414-85-1
• Molecular Formula: C7H13NO4
• Molecular Weight: 175.18
• Mol File: 127414-85-1.mol

Chemical Properties

• Boiling Point: 341°C at 760 mmHg
• Flash Point: 179.2°C
• Appearance: /
• Density: 1.722
• Vapor Pressure: 5.47E-06mmHg at 25°C
• Refractive Index: 1.714
• CAS DataBase Reference: calystegine B(2)(CAS DataBase Reference)
• NIST Chemistry Reference: calystegine B(2)(127414-85-1)
• EPA Substance Registry System: calystegine B(2)(127414-85-1)

Safety Data

• Hazardous Substances Data: 127414-85-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Calystegine B(2) is used as a therapeutic agent for the treatment of diabetes and obesity. Its ability to inhibit glycosidase enzymes helps regulate blood sugar levels and prevent the absorption of excess carbohydrates, offering a potential solution for managing these metabolic disorders.
Used in Neuroprotective Applications:
Calystegine B(2) is utilized as a neuroprotective agent to safeguard against neurotoxicity and reduce the risk of neurodegenerative diseases. Its potential role in protecting the nervous system and mitigating the impact of neurodegenerative conditions is currently under investigation, highlighting its promise as a future therapeutic intervention in the field of neurology.

InChI:InChI=1/C7H13NO4/c9-4-3-1-2-7(12,8-3)6(11)5(4)10/h3-6,8-12H,1-2H2/t3?,4-,5+,6-,7?/m0/s1

Upstream product

• 146176-80-9 (1R,2R,3R,4S,5R)-5-Azido-2,3,4-tris-benzyloxy-cycloheptanol 
• 146176-85-4 (3aR,5R,6R,7R,8S)-6,7,8-Tris-benzyloxy-5-methoxymethoxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole 
• 146176-77-4 (2R,3S,4R,5R,7S)-2,3,4-Tris-benzyloxy-7-hydroxymethyl-5-methoxymethoxy-cycloheptanone 
• 146176-74-1 (2R,3S,4R,5R)-2,3,4-Tris-benzyloxy-7-chloro-5-methoxymethoxy-cycloheptanone 
• 146176-78-5 (2R,3S,4R,5R)-2,3,4-Tris-benzyloxy-5-methoxymethoxy-cycloheptanone 
• 146176-79-6 (1S,2S,3R,4R,5R)-2,3,4-Tris-benzyloxy-5-methoxymethoxy-cycloheptanol 
• 141077-21-6 (3aR,5R,6R,7R,8S)-6,7,8-Tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazol-5-ol 
• 159639-21-1 (2S,3R,4S,5S) 5-mesyloxy-2,3,4-tris(benzyloxy) cyclohept-6,7-en-1-one 
• 146514-64-9 (2S,3R,4S,5S) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohept-6,7-en-1-one 
• 159639-22-2 (1R,2S,3R,4S,5S) 5-mesyloxy-2,3,4-tris(benzyloxy) cyclohept-6,7-en-1-ol 
• 159639-23-3 (1R,2S,3R,4S,5R) 5-azido-2,3,4-tris(benzyloxy) cyclohept-6,7-en-1-ol 
• 159639-20-0 (2S,3R,4S,5S) 5-hydroxy-2,3,4-tris(benzyloxy) cyclohept-6,7-en-1-one 
• 131289-28-6 (2S,3R,4R,5S) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one 
• 85716-45-6 1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon 

Relevant articles and documents

Concise synthesis of calystegines B2 and B3: Via intramolecular Nozaki-Hiyama-Kishi reaction

The key step in the concise syntheses of calystegine B2 and its C-2 epimer calystegine B3 was the construction of cycloheptanone 8via an intramolecular Nozaki-Hiyama-Kishi (NHK) reaction of 9, an aldehyde containing a Z-vinyl iodide. Vinyl iodide 9 was obtained by the Stork olefination of aldehyde 10, derived from carbohydrate starting materials. Calystegines B2 (3) and B3 (4) were synthesized from d-xylose and l-arabinose derivatives respectively in 11 steps in excellent overall yields (27% and 19%).

Synthesis of nortropane alkaloid calystegine B2 from methyl α-D-xylopyranoside

A new synthetic route for formation of a central cycloheptanone intermediate leading to the nortropane alkaloid calystegine B2 is described. The approach installs the desired ketone functionality directly in a ring-closing metathesis step. The

A short synthetic route to the calystegine alkaloids

An efficient strategy is described for the synthesis of enantiopure calystegine alkaloids. The key step employs a zinc-mediated fragmentation of benzyl-protected methyl 6-iodo-glycosides followed by in situ formation of the benzyl imine and Barbier-type allylation with zinc, magnesium, or indium metal. Stereochemistry in the pivotal allylation is controlled by the choice of the metal. The functionalized 1,8-nonadienes, thus formed, are converted into cycloheptenes by ring-closing olefin metathesis. Regioselective hydroboration and oxidation give the corresponding cycloheptanones, which are deprotected to afford the desired calystegines. Hereby, calystegine B2, B3, and B4 are prepared from D-glucose, D-galactose, and D-mannose, respectively. This route constitutes the shortest synthesis of calystegine B2 and gives rise to the first total syntheses of calystegine B3 and B4.

Short syntheses of enantiopure calystegine B2, B3, and B4

Calystegine B2, B3, and B4 have been prepared in 5 steps from the benzyl protected methyl 6-iodoglycopyranosides of glucose, galactose and mannose, respectively, by using a zinc-mediated domino reaction followed by ring-cl

A short and efficient synthesis of (+)-calystegine B2

A short synthesis of (+)-calystegine B2 from (D)-glucose has been achieved, which involves as the key step a triple domino zinc-mediated reductive ring-opening, imine formation and allylation reaction of 6-iodoglucopyranose.

General access to polyhydroxylated nortropane derivatives through hetero Diels-Alder cycloadditions. Part 3: Synthesis of natural (+)-calystegine B2

Cycloaddition of chiral nitroso derivatives with cyclohepta-1,3-diene gave one single stereoisomer with an excellent selectivity. The structures including absolute configurations have been assigned by spectroscopy and X-ray crystallography. These studies have been applied to the total synthesis of the naturally occurring calystegine B2.

Enantioselective syntheses of polyhydroxylated nortropane derivatives: Total synthesis of (+) and (-)-calystegine B2

(+) and (-)-Calystegine B2 were prepared from D-Glucose via Ferrier reaction followed by regiospecific ring enlargement of a polysubstituted cyclohexanone and intramolecular cyclisation of 4-aminocycloheptanone.

Polyhydroxylated nortropanes starting from D-glucose: Synthesis of homochiral (+) and ( -)-Calystegines B2

The cycloheptano-isoxazoline 1, prepared from D-glucose, is converted to 6,7-dideoxy cycloheptitols which are suitable precursors for the synthesis of enantiomerically pure (+) and (-)-Calystegines B2.