272113-59-4

Basic information

• Product Name: (-)-(1R,2R,4S,6S,2'S)-1-[Bis(benzyloxy)phosphoryloxy]-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane
• Synonyms: (-)-(1R,2R,4S,6S,2'S)-1-[Bis(benzyloxy)phosphoryloxy]-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane
• CAS NO: 272113-59-4
• Molecular Weight: 812.94
• Mol File: 272113-59-4.mol

Chemical Properties

• CAS DataBase Reference: (-)-(1R,2R,4S,6S,2'S)-1-[Bis(benzyloxy)phosphoryloxy]-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R,2R,4S,6S,2'S)-1-[Bis(benzyloxy)phosphoryloxy]-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane(272113-59-4)
• EPA Substance Registry System: (-)-(1R,2R,4S,6S,2'S)-1-[Bis(benzyloxy)phosphoryloxy]-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane(272113-59-4)

Safety Data

• Hazardous Substances Data: 272113-59-4(Hazardous Substances Data)

Upstream product

• 272113-57-2 (-)-(1R,2R,4S,6S,2'S)-1-(Diphenoxyphosphoryloxy)-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 140363-96-8 (+)-(1S,2R,4R,6R)-4-Benzyloxy-1,6-epoxycyclohexan-2-ol 
• 163878-18-0 (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane 
• 186703-35-5 (-)-(1R,2R,4R,6R)-1,2-Cyclohexylidenedioxy-6-(4'-methylphenylsulfonyloxy)cyclohexan-4-ol 
• 272113-50-5 (-)-(1R,2R,4R,6R)-4-Benzyloxy-6-(4'-methylphenylsulfonyloxy)cyclohexane-1,2-diol 
• 186703-36-6 (-)-(1R,2R,4R,6R)-1,2-Cyclohexylidenedioxy-4-benzyl-6-(4'-methylphenylsulfonyloxy)cyclohexane 
• 186703-34-4 (-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane 
• 186703-33-3 (-)-(1S,2R,4S,6R)-1,2-cyclohexyldienedioxy-4-(tert-butyldiphenylsilyloxy)cyclohexan-6-ol 
• 272113-55-0 (-)-(1R,2R,4S,6S,2'S)-2,4-Bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexanol 

Relevant articles and documents

Synthesis of (+)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol, a key precursor to inositol monophosphatase inhibitors, from (-)-quinic acid

A new and efficient route to homochiral (+)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol and its 2-benzyl ether derivative is described, starting from (-)-quinic acid. The compounds are key intermediates in the solution-phase and solid-phase synthesis of inhibitors for inositol monophosphatase. The pivotal step involves a La3+-induced reversal of the diastereoselectivity for the borohydride reduction of an intermediate cyclohexan-4-one. (1R,2R,4R,6R)-(O6-Propyl)cyclohexane-1,2,4,6-tetraol 1-phosphate, predicted to be a submicromolar competitive inhibitor of inositol monophosphatase, was prepared from the title epoxide in 5 steps in good overall yield. The compound proved to be a competitive inhibitor and displayed the expected potency confirming the stereochemical requirements for inhibition. The O2-benzylated epoxide derivative could be stereospecifically alcoholysed using either BF3·(OEt)2 or Yb(III)(OTf)3 as catalysts without appreciable levels of benzyl ether protecting group cleavage. The preparation of the alcoholysis products (1S,2R,4S,6R)-2,4-bis(benzyloxy)-6-isopropyloxycyclohexanol and (1S,2R,4S,6R)-2,4-bis(benzyloxy)-6-(phenethyloxy)cyclohexanol, and the synthesis and evaluation of the inhibitor (1R,2R,4R,6R,2′S)-6-(1′-hydroxy-3′-phenylpropan-2-yloxy)-2,4-d ihydroxycyclohexyl phosphate and its diastereomer (1R,2R,4R,6R,2′R)-6-(1′-hydroxy-3′-phenylpropan-2-yloxy)-2,4-d ihydroxycyclohexyl phosphate are described.