94903-42-1

Basic information

• Product Name: (1R,2R,4R,6R,8S)-8-Hydroxy-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undecan-9-one
• CAS NO: 94903-42-1
• Molecular Weight: 262.262
• Mol File: 94903-42-1.mol

Chemical Properties

• CAS DataBase Reference: (1R,2R,4R,6R,8S)-8-Hydroxy-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undecan-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,4R,6R,8S)-8-Hydroxy-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undecan-9-one(94903-42-1)
• EPA Substance Registry System: (1R,2R,4R,6R,8S)-8-Hydroxy-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undecan-9-one(94903-42-1)

Safety Data

• Hazardous Substances Data: 94903-42-1(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 77-95-2 (1R,3R,4S)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 183134-50-1 (2R,3aR,5R,7R,7aS)-5-Benzyloxycarbonyloxy-7-hydroxy-2-phenyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 183134-51-2 (2R,3aR,5S,7aS)-5-Benzyloxycarbonyloxy-2-phenyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 183134-53-4 (1R,4S)-1,4-Dihydroxy-3-oxo-cyclohexanecarboxylic acid 
• 183134-52-3 methyl (1R,3R,4S)-1,3,4-trihydroxycyclohexane-1-carboxylate 
• 183254-43-5 (1R,3R,4S)-1,3,4-Trihydroxy-cyclohexanecarboxylic acid 
• 183254-44-6 (S)-4-Hydroxy-3-oxo-cyclohex-1-enecarboxylic acid 
• 183134-49-8 Carbonic acid benzyl ester (1R,2R,4R,6R,8S)-9-oxo-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undec-8-yl ester 
• 94903-41-0 (-)-methyl 4,5-O-benzylidene-4-epi-shikimate 
• 94903-43-2 (1S,2S,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-en-2-ol 
• 94843-97-7 (1R,2R,6R,8S)-2-(benzoyloxy)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene 
• 94843-96-6 (1S,4S,6R,8S)-4-(methoxycarbonyl)-2-oxo-8-phenyl-7,9-dioxabicyclo<4.3.0>nonan-4-ol 
• 21967-35-1 (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 94843-95-5 (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol 

Relevant articles and documents

Synthesis of (2R)-2-bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid

(2R)-2-Bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid ? have each been synthesised in six steps from quinic acid via the common intermediate 6. The syntheses exploit the selective protection of the 4-hydroxy group of the quinic acid lactone 3 with tert-butyldimethylsilyl chloride. ? IUPAC names: (1S,2R,4S,5R)-2-bromo-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid and (1S,2R,4S,5R)-2-fluoro-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid, respectively.

Comparison of the substrate specificity of type I and type II dehydroquinases with 5-deoxy- and 4,5-dideoxy-dehydroquinic acid

Syntheses of 5-deoxydehydroquinic acid and 4,5-dideoxydehydroquinic acid from quinic acid are described. These substrate analogues were tested against the mechanistically-distinct type I and type II dehydroquinases. The C-4 hydroxy group of the substrate is shown to be important for imine formation on the type I enzyme but appears not to contribute significantly to specificity on the type II dehydroquinase.