484-69-5

Basic information

• Product Name: 6α-Methoxycyclohexane-1β,2β,3β,4α,5β-pentol
• Synonyms: (+)-Ononitol;4-O-Methyl-myo-inositol;Ononitol
• CAS NO: 484-69-5
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18246
• Mol File: 484-69-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6α-Methoxycyclohexane-1β,2β,3β,4α,5β-pentol(CAS DataBase Reference)
• NIST Chemistry Reference: 6α-Methoxycyclohexane-1β,2β,3β,4α,5β-pentol(484-69-5)
• EPA Substance Registry System: 6α-Methoxycyclohexane-1β,2β,3β,4α,5β-pentol(484-69-5)

Safety Data

• Hazardous Substances Data: 484-69-5(Hazardous Substances Data)

Upstream product

• 642-38-6 quebrachitol 
• 111392-29-1 (3aS,4S,4aS,7aS,8S,8aR)-4-Allyloxy-8-methoxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 71-43-2 benzene 
• 98510-20-4 myo-Inositol orthoformate 
• 124647-07-0 C₂₁H₂₂O₈ 
• 111392-26-8 (3aS,4S,4aR,7aR,8S,8aR)-4-Methoxy-8-(4-methoxy-benzyloxy)-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 111392-30-4 1-O-allyl-4-O-methyl-myo-inositol 
• 111015-73-7 DL-1,2-di-O-methyl-chiro-inositol 
• 111015-74-8 DL-1,3-di-O-benzoyl-4-O-methyl-chiro-inositol 
• 111015-72-6 (1α,2β,3β,6β)-6-methoxy-4-cyclohexene-1,2,3-triol 2,3-dibenzoate 
• 80971-00-2 (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 111446-91-4 (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol 
• 98906-29-7 (1R,2S,3R,4R,5S,6R)-2,4,5-Tris-allyloxy-3,6-bis-benzyloxy-cyclohexanol 
• 98906-26-4 (3aR,4R,5S,6S,7R,7aS)-5,6-Bis-allyloxy-4,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 

Downstream Products

• 14199-75-8 (1R,2S,3R,4R,5S,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane 
• 54324-59-3 2,3,4,5,6-Penta-O-acetyl-1-O-methyl-myo-inositol 

Relevant articles and documents

Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis

Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics

Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

Mikrobial Oxidation in Synthesis: Preparation of (+)- and (-)-Pinitol from Benzene

Microbial oxidation with Pseudomonas putida of benzene affords cis-1,2-dihydroxycyclohexa-3,5-diene (2) which may be converted in five steps and 49percent overall yield to (+/-)-pinitol.Resolution of an intermediate alcohol (6) with menthoxyacetyl chloride provides optically pure materials which may be independently transformed to (+)- or (-)-pinitol.Demethylation conditions for pinitol together with further reactions of (2) and related compounds were investigated.