18424-51-6

Basic information

• Product Name: (1R)-cyclohexane-1r,2c,3c,4t-tetraol
• Synonyms: (1R)-cyclohexane-1r,2c,3c,4t-tetraol
• CAS NO: 18424-51-6
• Molecular Weight: 148.159
• Mol File: 18424-51-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (1R)-cyclohexane-1r,2c,3c,4t-tetraol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-cyclohexane-1r,2c,3c,4t-tetraol(18424-51-6)
• EPA Substance Registry System: (1R)-cyclohexane-1r,2c,3c,4t-tetraol(18424-51-6)

Safety Data

• Hazardous Substances Data: 18424-51-6(Hazardous Substances Data)

Upstream product

• 20089-20-7 (+/-)-trans-1,2-Dihydroxy-3-cyclohexene 
• 277-06-5 cyclohexa-1,3-diene diepoxide 
• 526-87-4 (+/-)-Conduritol B 
• 7732-18-5 water 
• 1165952-91-9 cyclohexa-1,3-diene 
• 139013-56-2 (1R,4R,5S,6S)-1-chloro-7,8-dioxa-5,6-di-O-isopropylidenebicyclo<2.2.2>oct-2-ene 
• 127666-06-2 (3aS,7aS)-4-chloro-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 198628-65-8 (-)-(1S,2S,3R,4R)-3,4-(cyclohexylidenedioxy)-2-methoxycyclohexan-1-ol 
• 159191-08-9 (-)-(2R,3R,4R)-3,4-(cyclohexylidenedioxy)-2-methoxycyclohexan-1-one 
• 98485-58-6 (2S)-2r,3c,4t-trihydroxy-cyclohexanone 
• 2975-92-0 (1R,2R,3R,4R)-cyclohexane-1,2,3,4-tetrol 
• 139013-59-5 (1R,2R,3R,4R)-1-hydroxy-2,3-di-O-isopropylidene-4-O-(t-butyldimethylsilyl)cyclohexane 
• 123238-09-5 (1R,2R,3S,4R)-cyclohex-5-ene-1,2,3,4-tetrol 
• 2975-92-0 d,l-(1,2,3/4)-cyclohexanetetrol 

Downstream Products

• 2975-92-0 (1R,2R,3R,4R)-cyclohexane-1,2,3,4-tetrol 
• 18422-12-3 (1R)-cyclohexane-1r,2c,3t,4c-tetraol 
• 2975-92-0 (+/-)-cyclohexane-1r,2c,3t,4t-tetraol 
• 2975-92-0 (+/-)-1L-cyclohexane-1,3/2,4-tetrol 
• 20021-56-1 DL-(1,3/2,4)-1,2,3,4-Tetra-O-acetylcyclohexanetetrol 
• 20021-56-1 cyclohexane-r-1,c-2,t-3,t-4-tetrayl tetraacetate 
• 20021-56-1 (+/-)-1D-tetra-O-acetylcyclohexane-1,2,4/3-tetrol 
• 18422-07-6 (+/-)-1r,2c,3c,4t-tetrakis-benzoyloxy-cyclohexane 
• 18422-07-6 (+/-)-1r.2t.3c.4t-tetrabenzoyloxy-cyclohexane 
• 18422-07-6 (+/-)-1r,2c,3t,4c-tetrakis-benzoyloxy-cyclohexane 
• 18422-07-6 (1R)-1r,2c,3c,4t-tetrakis-benzoyloxy-cyclohexane 

Relevant articles and documents

Dihydroxylation of polyenes using Narasaka's modification of the upjohn procedure

Dihydroxylation of a variety of commercially available polyenes has been investigated using phenylboronic acid, .ZV-methylmorpholine Af-oxide (NMO), and osmium tetroxide in anhydrous solvent. The diastereoselectivity of multiple oxidation steps is in some cases affected by the in situ protection of the intermediate ene-diols as phenyboronic esters, affording polyols not available from the standard Upjohn dihydroxylation procedure. A convenient oxidative deprotection of the phenylboronic esters is also described.

Facile stereoselective syntheses of four of the six 1, 2, 3, 4-cyclohexanetetrols: Increasing the accessibility of cyclitols for probing the molecular recognition of saccharides

New and stereoselective syntheses of (1,2,3/4)-, (1,2/3,4)-, (1,4/2,3)-, and (1,2,4/3)-cyclohexanetetrols (1,2,3 and 4 respectively) are described. The known syn and anti 1,4-cyclohex-2-enediols 9 and 10 were used as starting materials. Diols 9 and 10 wer

Biocatalysis as a Rational Approach to Enantiodivergent Synthesis of Highly Oxygenated Compounds: (+)- and (-)-Pinitol and Other Cyclitols

Bacterial oxygenation of halogenated aromatic compounds yields arene cis-diols of type 2 of high enantiomeric purity.Further oxygenation of these extremely versatile synthetic intermediates provides for stereo- and regioselective introduction of additional functionalities such as hydroxyl groups.Several rational methods of oxygenation (epoxidation, osmylation, singlet oxygen addition, and ozonolysis) are used to produce, in short synthetic routes, cyclitol derivatives of medicinal importance.Proper symmetry considerations lead to the development of enantiodivergent synthetic design of target compounds from a single enantiomer of a starting diol.These principles are ilustrated on the short syntheses of (+)- and (-)-pinitol.Stereocontrolled oxidative transformation of diols of type 2 are exemplified in the synthesis of conduritol C and dihydroconduritol C.Full experimental details are provided for all compounds.A guide to the stereorational design of any stereoisomer of cyclohexane (poly)ols or carbohydrates is provided at the end of the paper.