148218-11-5

Basic information

• Product Name: (2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexanone
• Synonyms: (2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexanone
• CAS NO: 148218-11-5
• Molecular Weight: 178.142
• Mol File: 148218-11-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexanone(148218-11-5)
• EPA Substance Registry System: (2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexanone(148218-11-5)

Safety Data

• Hazardous Substances Data: 148218-11-5(Hazardous Substances Data)

Upstream product

• 319-89-1 tetrahydroxy-1,4-quinone 
• 1607827-84-8 (2S,3S,4R,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexanone 
• 127666-06-2 (3aS,7aS)-4-chloro-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 86992-79-2 (1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol 
• 497162-79-5 (2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-2,6-dimethoxy-tetrahydro-pyran-4-ol 
• 497162-84-2 (2R,3R,4R,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-2,6-dimethoxy-tetrahydro-pyran-4-ol 
• 497162-81-9 2,4,6-tri-O-benzyl-L-lyxo-hexos-5-ulose 
• 497162-80-8 2,6-di-O-benzyl-L-lyxo-hexos-5-ulose 
• 216577-78-5 methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside 
• 134039-09-1 methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside 
• 497162-83-1 (2R,3S,4S,5S,6S)-2,4,6-Tris-benzyloxy-3,5-dihydroxy-cyclohexanone 
• 497162-82-0 2,4-di-O-benzyl-2L-(2,3,4,5,6)-pentahydroxycyclohexanone 
• 148132-86-9 (1R,2S,3S,4R,5S,6S)-1-Chloro-3,4-dihydroxy-5,6-di-O-isopropylidene-1,2-epoxycyclohexane 
• 87-89-8 D-myo-inositol 

Downstream Products

• 1254-38-2 inositol peracetate 
• 20108-71-8 hexa-O-acetyl-epi-inositol 
• 87-89-8 D-myo-inositol 
• 488-58-4 epi-Inositol 
• 643-10-7 allo-inositol 
• 24924-09-2 1,2,3,5-tetraacetoxy-benzene 

Relevant articles and documents

General Synthesis of Inositols by Hydrolysis of Conduritol Epoxides Obtained Biocatalytically from Halogenobenzenes: (+)-D-chiro-Inositol, allo-Inositol, muco-Inositol and neo-Inositol

Four of the nine isomeric inositols have been prepared by hydrolytic opening of epoxides derived from 3-halogenocyclohexa-3,5-diene-1,2-diol by further oxidation with potassium permanganate or by reduction of chiro-3-inosose (2L-2,3,6/4,5-pentahydroxycyclohexanone).

Protecting group directed stereoselective reduction of an epi-inosose: Efficient synthesis of epi-inositol

A facile and high yielding synthesis of epi-inositol via stereoselective reduction of a pentaprotected epi-inosose is reported. Extent of stereoselectivity during the hydride reduction appears to depend on the ability of the substrate to complex with metal ions in the reducing agent.

Intramolecular aldol cyclization of L-lyxo-hexos-5-ulose derivatives: A new diastereoselective synthesis of D-chiro-inositol

The DBU-promoted intramolecular aldol condensation of two partially protected L-lyxo-hexos-5-ulose derivatives (8 and 9), in turn obtained starting from methyl β-D-galactopyranoside, takes place with fairly good yield and complete diastereoselectivity to