131580-36-4

Basic information

• Product Name: calystegine A3
• Synonyms: calystegine A3;Calystegin A3;(1R,2S,3R,5R)-8-Azabicyclo[3.2.1]octane-1,2,3-triol
• CAS NO: 131580-36-4
• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.18302
• Mol File: 131580-36-4.mol

Chemical Properties

• Boiling Point: 296.9°Cat760mmHg
• Flash Point: 153.1°C
• Appearance: /
• Density: 1.52g/cm³
• Vapor Pressure: 0.000143mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: calystegine A3(CAS DataBase Reference)
• NIST Chemistry Reference: calystegine A3(131580-36-4)
• EPA Substance Registry System: calystegine A3(131580-36-4)

Safety Data

• Hazardous Substances Data: 131580-36-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Calystegine A3 is used as a therapeutic agent for the treatment of type 2 diabetes. Its presence in potato cultivars can be influenced by external factors such as wounding, light, and heat treatments, which may have implications for its potential use in diabetes management.

InChI:InChI=1/C7H13NO3/c9-5-3-4-1-2-7(11,8-4)6(5)10/h4-6,8-11H,1-3H2/t4-,5-,6+,7-/m1/s1

Upstream product

• 1352406-27-9 (1R,2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxy-1-O-triisopropylsilyloxycycloheptane 
• 1352406-28-0 (1R,2R,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptan-1-ol 
• 1352406-29-1 (2S,3R,5R)-5-azido-3-O-benzyloxy-2-O-p-methoxybenzyloxycycloheptanone 
• 1352406-30-4 (1R,2S,3R,5R)-3-O-benzyloxy-2-O-p-methoxybenzyloxy-8-azabicyclo[3.2.1]octane-1-ol 
• 1184705-70-1 (2S,3R,5R)-5-[(benzyl)(benzyloxycarbonyl)amino]-2,3-bis(benzyloxy)cycloheptanone 

Relevant articles and documents

Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation

Calystegine A3 is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-d-glucose applying a diastereoselective allylation protocol.

Synthesis of calystegine A3 from glucose by the use of ring-closing metathesis

A synthesis of the nortropane alkaloid calystegine A3 is described from D-glucose. The key step employs a zinc-mediated tandem reaction where a benzyl-protected methyl 6iodo glucoside is fragmented to give an unsaturated aldehyde, which is then transformed into the corresponding benzylimine and allylated in the same pot. The functionalized nona-l,8-diene, thus obtained, is converted into the sevenmembered carbon skeleton in calystegine A3 by ring-closing olefin metathesis. Subsequent deoxygenation by the BartonMcCombie protocol, hydroboration and oxidative workup followed by hydrogenolysis affords calystegine A3. The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product.