32384-44-4

Basic information

• Product Name: (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone
• Synonyms: (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone
• CAS NO: 32384-44-4
• Molecular Weight: 262.262
• Mol File: 32384-44-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone(32384-44-4)
• EPA Substance Registry System: (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone(32384-44-4)

Safety Data

• Hazardous Substances Data: 32384-44-4(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 94843-95-5 (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol 
• 105539-78-4 (1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate 
• 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 
• 124561-23-5 (3R,4S,5R)-3,4-O,O'-benzylidene-1-(hydroxymethyl)cyclohexane-1,3,4,5-tetrol 

Relevant articles and documents

Application of stereocontrolled aldol coupling to synthesis of segments of immunosuppressants FK-506 and rapamycin

The sector comprising C24-C34 of FK-506 containing five of the stereogenic centers in this macrolide was synthesized from (-)-quinic acid. Aldol coupling of the C24-C34 unit with a methyl ketone representing C20-C23 of FK-506 proceeded with complete Felkin stereoselectivity to afford the C20-C34 portion of the immunosuppressant. A chelate transition state invoking coordination of a lithium enolate with a trityl ether is proposed to explain this stereoselectivity. The strategy adopted for construction of the C26-C34 moiety of FK-506 was extended to the C34-C42 subunit of rapamycin. A Mukaiyama asymmetric anti-aldol coupling was used to set in place the vicinal diol functionality at C27,28 in the C26-C33 segment of this macrolide.

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.

(-)-Methyl 4,5-Benzylidene-4-epi-shikimate: An Intermediate for the Synthesis of (-)-Chorismic Acid and Analogues

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