81369-59-7

Basic information

• Product Name: 3-deoxy-epi-inositol
• Synonyms: 3-deoxy-epi-inositol
• CAS NO: 81369-59-7
• Molecular Weight: 164.158
• Mol File: 81369-59-7.mol

Chemical Properties

• CAS DataBase Reference: 3-deoxy-epi-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deoxy-epi-inositol(81369-59-7)
• EPA Substance Registry System: 3-deoxy-epi-inositol(81369-59-7)

Safety Data

• Hazardous Substances Data: 81369-59-7(Hazardous Substances Data)

Upstream product

• 81562-18-7 3-O-benzyl-1,2,4,5/3-cyclohexanepentol 
• 215026-25-8 (1S,3S,4S,6R,7S,8R,9R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]decane-7,8,9-triol 
• 849596-75-4 (1R,2R,3S,4R,5S)-5-benzyloxy-4-(tert-butyl-diphenylsilanyloxy)-cyclohexane-1,2,3-triol 
• 20097-36-3 (1R,2R,3R,4S,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 
• 256240-09-2 (1S,2S,3S)-cyclohex-4-en-1,2,3-triol 
• 256240-08-1 (1R,2R,3R)-cyclohex-4-en-1,2,3-triol 
• 849596-59-4 (1S,3S,4R)-3-phenyl-4a,7,8,8a-tetrahydro-benzo[1,4]dioxin-2-one 
• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 125477-54-5 conduritol A terabenzoate 
• 18376-41-5 DL-proto-quercitol pentaacetate 
• 18376-41-5 rac-(1R,2S,3R,4S,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 
• 34361-62-1 1-O-benzoyl-2,3:4,5-di-O-cyclohexylidene-epi-enositol 
• 1521-51-3 rac-3-bromocyclohexene 
• 849596-68-5 (1S,2R,1'S)-2-(1-phenyl-2-phenylselanyl-ethoxy)-cyclohex-3-enol 

Downstream Products

• 20021-56-1 DL-(1,3/2,4)-1,2,3,4-Tetra-O-acetylcyclohexanetetrol 
• 6216-28-0 DL-(1,3,5/2,4)-1-Acetamido-2,3,4,5-tetra-O-acetylcyclohexanetetrol 
• 2975-92-0 (+/-)-1L-cyclohexane-1,3/2,4-tetrol 
• 18376-41-5 rac-(1R,2S,3R,4S,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 
• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 20097-36-3 (1R,2R,3R,4S,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 
• 22144-52-1 (+/-)-3r,4t,5c-trihydroxy-cyclohexane-1,2-dione-bis-phenylhydrazone 

Relevant articles and documents

Stereoselective syntheses of racemic quercitols and bromoquercitols starting from cyclohexa-1,4-diene: Gala-, epi-, muco-, and neo-quercitol

The efficient synthesis of gala-, epi-, neo-, and muco-quercitols and some brominated quercitols starting from cyclohexa-1,4-diene is reported. Treatment of the dibromide, obtained by the addition of bromine to cyclohexa-1,4-diene, with m-chloroperbenzoic

Epoxidation of protected (1,4,5)-cyclohex-2-ene-triols and their acid hydrolysis to synthesize quercitols from D-(-)-quinic acid

Highly stereoselective epoxidations have been achieved in both cyclohexylidene acetal and butane 2,3-bisacetal (BBA) protection of (1,4,5)-cyclohex-2-ene-triols. These epoxy derivatives are all derived from D-(-)-quinic acid and can be used for the synthe

Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S,S)-hydrobenzoin and (S)-mandelic acid as chiral sources

Reaction of 3-bromocyclohexene with (S,S)-hydrobenzoin and (S)-mandelic acid and subsequent intramolecular oxyselenenylation of the resulting allylic ethers followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefins, (1S,3S,4S,6R)-3,4-diphenylbicyclo[4,4,0]-2,5-dioxa-7-decene and (1S,3S,4R)-3-phenyl-4a,7,8,8a-tetrahydro-benzo[1,4]dioxan-2-one, respectively. Further stereoselective transformation of these cis-fused bicyclic olefins afforded the enantiopure cyclohexitols, muco-quercitol, D-chiro-inocitol and allo-inocitol.

An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene

gala-Quercitol was synthesized from 1,4-cyclohexadiene in seven steps and overall yield of 68%. Reaction of 5,6-dibromo-2,2-dimethylhexahydro-1,3-benzodioxole, synthesized from 1,4-cyclohexadiene in three steps, with excess NaOMe gave (3aα,5α,7aα)-5-metho

Carbohydrate carbocyclization by a novel zinc-mediated domino reaction and ring-closing olefin metathesis

A general method for carbocyclization of carbohydrates is described using two consecutive organometallic transformations: a novel zinc-mediated domino reaction to give functionalized dienes followed by ring-closing olefin metathesis. In the first reaction

Transformation of cyclohexene to enantiopure cyclitols mediated by sequential oxyselenenylation with (S,S)-hydrobenzoin: Synthesis of D-chiro-inositol and muco-quercitol

Oxyselenenylation of cyclohexene with (S,S)-hydrobenzoin and subsequent oxidation-elimination allows isolation of an allylic ether in which further phenylselenenylation is completely regioselective, thus allowing entry to the cyclitols D-chiro-inositol and muco-quercitol.

An Advantageous Synthesis of 1D- and 1L-1,2,3,5/4-Cyclohexanepentol

The title compounds D-10 and L-10 were prepared from 1 in eight steps and in a combined overall yield of 41-49%.

A novel synthesis of DL-proto-, and DL-vibo- quercitol via 1,4- cyclohexadiene

Photooxygenation of 1,4-cyclohexadiene 3 followed by reduction with LiAIH4 or thiourea gave (25/1)-cyclohex-3-ene-triol 7a. trans-Hydroxylation of triol 7a with three different methods afforded both of proto-quercitol 1a and vibo-quercitol 2a.

A concise and convenient synthesis of DL-proto-quercitol and DL-gala-quercitol via ene reaction of singlet oxygen combined with [2 + 4] cycloaddition to cyclohexadiene

Photooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxides 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH4 or thiourea followed by acetylation of the hydroxyl group and KMnO4 oxidation of the double bond gave proto-quercitol 10b. Application of the same reaction sequences to 4 resulted in the formation of gala-quercitol 14. Quercitols were easily obtained by ammonolysis of acetate derivatives in MeOH. The outcome of dihydroxylation reactions were supported by conformational analysis.