163878-18-0

Basic information

• Product Name: (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane
• Synonyms: (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane
• CAS NO: 163878-18-0
• Molecular Weight: 310.393
• Mol File: 163878-18-0.mol

Chemical Properties

• CAS DataBase Reference: (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane(163878-18-0)
• EPA Substance Registry System: (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane(163878-18-0)

Safety Data

• Hazardous Substances Data: 163878-18-0(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 186703-33-3 (-)-(1S,2R,4S,6R)-1,2-cyclohexyldienedioxy-4-(tert-butyldiphenylsilyloxy)cyclohexan-6-ol 
• 186703-34-4 (-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane 
• 186703-36-6 (-)-(1R,2R,4R,6R)-1,2-Cyclohexylidenedioxy-4-benzyl-6-(4'-methylphenylsulfonyloxy)cyclohexane 
• 272113-50-5 (-)-(1R,2R,4R,6R)-4-Benzyloxy-6-(4'-methylphenylsulfonyloxy)cyclohexane-1,2-diol 
• 186703-35-5 (-)-(1R,2R,4R,6R)-1,2-Cyclohexylidenedioxy-6-(4'-methylphenylsulfonyloxy)cyclohexan-4-ol 
• 406460-98-8 (1R,2R,3S,5R)-5-(tert-butyldimethylsiloxy)-2,3-epoxycyclohexanol 
• 357174-91-5 (1S,4S,6S)-4-(tert-butyldimethylsilyloxy)-7-oxa-bicyclo[4.1.0]heptan-2-one 
• 406461-01-6 (1S,3S,4S)-4,5-epoxy-3,3-dimethoxycyclohexanol 
• 406461-02-7 (2S,3S,5S)-2,3-epoxy-5-hydroxycyclohexanone 
• 406461-00-5 (1R,3R,4R,5S)-4,5-epoxycyclohexane-1,3-diol 
• 140363-96-8 (+)-(1S,2R,4R,6R)-4-Benzyloxy-1,6-epoxycyclohexan-2-ol 

Downstream Products

• 218915-50-5 (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-6-aminocyclohexanol 
• 676327-51-8 (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-6-(N-benzyloxycarbonyl-2-aminoethyl)cyclohexanol 
• 676327-47-2 (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-6-{N-(4-phenylbutyl)-N-[(N'-benzyloxycarbonyl)-2-aminoethyl]amino}cyclohexanol 
• 696640-67-2 (-)-(1S,2R,4S,6R)-2,4,6-tris(benzyloxy)cyclohexanol 
• 186703-40-2 (-)-(1R,2R,4R,6R)-6-Propoxy-2,4-dihydroxycyclohexyl phosphate 
• 186703-39-9 (-)-(1S,2R,4S,6R)-1-[Bis(benzyloxy)phosphoryloxy]-2,4-bis(benzyloxy)-6-propyloxycyclohexe 
• 218915-58-3 [(1R,2S,3R,5S)-3,5-Bis-benzyloxy-2-(bis-benzyloxy-phosphoryloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester 
• 218915-57-2 [(1R,2S,3R,5S)-3,5-Bis-benzyloxy-2-(bis-benzyloxy-phosphoryloxy)-cyclohexyl]-carbamic acid benzyl ester 
• 218915-53-8 ((1R,2S,3R,5S)-3,5-Bis-benzyloxy-2-hydroxy-cyclohexyl)-carbamic acid benzyl ester 
• 218915-60-7 6-methylamino-1,2,4-trihydroxycyclohexane 1-phosphate 
• 218915-59-4 6-amino-1,2,4-trihydroxycyclohexane 1-phosphate 
• 272113-60-7 (-)-(1R,2R,4S,6S,2'R)-1-[Bis(benzyloxy)phosphoryloxy]-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane 
• 272113-59-4 (-)-(1R,2R,4S,6S,2'S)-1-[Bis(benzyloxy)phosphoryloxy]-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane 
• 272113-58-3 (-)-(1R,2R,4S,6S,2'R)-1-(Diphenoxyphosphoryloxy)-2,4-bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexane 

Relevant articles and documents

Novel synthesis of enantiomerically enriched 5-hydroxycyclohex-2-enone by enantioselective deprotonation strategy: Application to the synthesis of inositol phosphatase inhibitor

A novel synthetic path to enantiomerically enriched 5-hydroxycyclohex-2-enone, a versatile chiral building block, is developed by a two-step sequence, where an enantioselective deprotonation of a 3,5-dihydroxycyclohexanone derivative with lithium (S,S′)-α

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.

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 (-)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol is described starting from (-)-quinic acid. 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)-6-Propyloxycyclohexan-1,2,4-triol 1-phosphate, predicted to be a submicromolar inhibitor of inositol monophosphatase, was prepared from the epoxide in 20% yield and displayed the expected potency.