286956-61-4

Basic information

• Product Name: methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate
• Synonyms: methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate
• CAS NO: 286956-61-4
• Molecular Weight: 372.418
• Mol File: 286956-61-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate(286956-61-4)
• EPA Substance Registry System: methyl (3R,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate(286956-61-4)

Safety Data

• Hazardous Substances Data: 286956-61-4(Hazardous Substances Data)

Upstream product

• 123994-31-0 methyl (3S,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate 
• 65-85-0 benzoic acid 

Downstream Products

• 286956-66-9 Acetic acid (1R,5R,6R)-5,6-diacetoxy-3-[(R)-(bis-allyloxy-phosphoryl)-hydroxy-methyl]-cyclohex-3-enyl ester 
• 286956-67-0 Acetic acid (1R,5R,6R)-5,6-diacetoxy-3-[(S)-(bis-allyloxy-phosphoryl)-hydroxy-methyl]-cyclohex-3-enyl ester 
• 286956-64-7 (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxy-N-methoxy-N-methylcyclohex-1-ene-1-carboxamide 
• 286956-63-6 (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 286956-65-8 (3R,4R,5R)-3,4,5-tri-O-acetyl-3,4,5-trihydroxycyclohex-1-ene-1-carbaldehyde 
• 21967-35-1 (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 286956-62-5 methyl (3R,4R,5R)-3-O-benzoyl-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate 

Relevant articles and documents

Sialyltransferase inhibitors based on CMP-quinic acid

Quinic acid was transformed into phosphitamides 16, 25, and 36, which could be readily linked to 5'-O-unprotected cytidine derivative 17. Ensuing oxidation of the obtained phosphite triesters with tBuO2H and hydrogenolytic de-O-benzylation furnished the corresponding phosphate diesters 18, 26, and 38. Base catalyzed removal of acetyl protecting groups, and methyl ester hydrolysis furnished CMP-Neu5Ac analogues 1d, 1e, and 2. Quinic acid was also transformed into 1,2-unsaturated diallyl α-hydroxymethyl-phosphate derivatives (R)- and (S)-46, which on reaction with cytidine phosphitamide 47 afforded the phosphite triesters. Subsequent oxidation with tBuO2H and then treatment with NEt3 gave phosphate diester derivatives (R)- and (S)-48. Deallylation, acetyl group removal, and methyl ester hydrolysis furnished (R)- and (S)-3, respectively. Treatment of (R)- and (S)-48 with DBU as a base led to acetic acid elimination, thus yielding, after de-O-allylation, acetyl group cleavage, and ester hydrolysis, diene derivative (E)-4. Donor substrate analogues 1d and 1e exhibited good α(2-6)-sialyltransferase inhibition (K(i): 2.0 · 10-4 and 2.0 · 10-5 M). However, transition state analogues (R)-, and particularly (S)-3 showed excellent inhibition properties (K(i): 1.6 · 10-6 and 2.7 · 10-7 M).