949887-66-5

Basic information

• Product Name: (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol
• Synonyms: (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol
• CAS NO: 949887-66-5
• Molecular Weight: 539.671
• Mol File: 949887-66-5.mol

Chemical Properties

• CAS DataBase Reference: (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol(949887-66-5)
• EPA Substance Registry System: (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol(949887-66-5)

Safety Data

• Hazardous Substances Data: 949887-66-5(Hazardous Substances Data)

Upstream product

• 949887-65-4 (+)-(1S,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 864948-63-0 (+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 950170-55-5 (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate 
• 6090-95-5 (+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane 
• 138258-55-6 (1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 949887-64-3 (1R,2R,3S,6S)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 
• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 

Downstream Products

• 1374772-01-6 (1S,2S,3S,4R,5S,6S)-6-(di-n-nonylamino)cyclohexane-1,2,3,4,5-pentaol hydrochloride 
• 1374772-02-7 (1S,2S,3R,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(di-n-nonylamino)cyclohexanol 
• 1287227-02-4 (3aS,4S,5R,6S,7R,7aS)-2-(nonylimino)-octahydrobenzo[d]oxazole-4,5,6,7-tetraol 
• 1287227-00-2 (3aS,4S,5S,6S,7R,7aS)-4-(benzyloxy)-2-(nonylimino)-octahydrobenzo[d]oxazole-5,6,7-triol 
• 1287225-92-6 1-nonyl-3-((1R,2S,3R,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexyl)thiourea 
• 1287225-55-1 (1S,2S,3R,4R,5S,6R)-2,3,4,5-tetrakis(benzyloxy)-6-(n-nonylamino)cyclohexanol 
• 1287226-46-3 N-((3aS,4S,5R,6S,7S,7aS)-4,5,6,7-tetrakis(benzyloxy)-3-nonyl-hexahydrobenzo[d]oxazol-2(3H)-ylidene)nonan-1-amine 
• 1287226-43-0 N-((3aS,4S,5R,6S,7S,7aS)-4,5,6,7-tetrakis(benzyloxy)-hexahydrobenzo[d]oxazol-2(3H)-ylidene)nonan-1-amine 
• 1287225-94-8 1,3-dinonyl-1-((1R,2S,3R,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexyl)thiourea 

Relevant articles and documents

Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors

A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs p-benzoquinone, an achiral compound, as the starting material to give conduritol B tetraacetate in three steps. Kinetic resolution of this compound using a palladium catalyst with a chiral ligand allows access to a conduritol B tetraester in high enantiomeric excess. This compound is transformed into tetrabenzyl conduritol B epoxide, which is regioselectively opened with azide to give the key azidocyclitol. Final transformation into (-)-1-amino-1-deoxy-myo-inositol hydrochloride is achieved in four synthetic steps. This sequence allows the synthesis of this compound in high enantiomeric purity in a semi-preparative scale.