202459-97-0

Basic information

• Product Name: 4-Cyclohexene-1,2,3-triol,6-amino-,[1S-(1alpha,2beta,3beta,6beta)]-(9CI)
• Synonyms: 4-Cyclohexene-1,2,3-triol,6-amino-,[1S-(1alpha,2beta,3beta,6beta)]-(9CI)
• CAS NO: 202459-97-0
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.16
• Product Categories: AMINEPRIMARY
• Mol File: 202459-97-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 283.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.477±0.06 g/cm3(Predicted)
• PKA: 13.70±0.70(Predicted)
• CAS DataBase Reference: 4-Cyclohexene-1,2,3-triol,6-amino-,[1S-(1alpha,2beta,3beta,6beta)]-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyclohexene-1,2,3-triol,6-amino-,[1S-(1alpha,2beta,3beta,6beta)]-(9CI)(202459-97-0)
• EPA Substance Registry System: 4-Cyclohexene-1,2,3-triol,6-amino-,[1S-(1alpha,2beta,3beta,6beta)]-(9CI)(202459-97-0)

Safety Data

• Hazardous Substances Data: 202459-97-0(Hazardous Substances Data)

Upstream product

• 163072-76-2 1D-(1,2,4/3)-4-(t-butoxycarbonyl)amino-1,2-O-isopropylidene-5-cyclohexene-1,2,3-triol 

Downstream Products

• 202459-98-1 1D-(1,2,4/3)-4-acetamido-1,2,3-tri-O-acetyl-5-cyclohexene-1,2,3-triol 

Relevant articles and documents

Total synthesis of acanthacerebroside A and astrocerebroside A via a chiral epoxide intermediate derived from L-quebrachitol

The chiral and stereoselective total synthesis of novel cerebrosides, acanthacerebroside A (1) and astrocerebroside A (2), isolated from starfish, is described. The phytosphingosine moieties in 1 and 2 were prepared by the coupling reaction of dialkylmagnesium reagents with the common epoxide intermediate, 2-(t-butoxycarbonyl)amino-1-O-(t-butyldiphenylsilyl)-2-deoxy- 3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol (5). The epoxide (5) was synthesized from naturally occurring cyclitol, L-quebrachitol via the conduramine derivative, which was prepared regio- and stereoselectively by the Pd-catalyzed azidation of the allyl carbonate derivative. Condensation of phytosphingosines with 2-acetoxy fatty acid residue, followed by glycosidation, furnished the total synthesis. This work established an effective synthetic pathway to a wide variety of cerebrosides containing various phytosphingosines and 2-hydroxy fatty acid residue; the first total synthesis of astrocerebroside A (2) fully confirmed the proposed structure.