3411-22-1

Upstream product

• 863224-35-5 (1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 
• 1165952-92-0 cyclohexa-1,4-diene 
• 125477-54-5 conduritol A terabenzoate 
• 130824-35-0 proto-quercitol tetramethyl ether 
• 18376-41-5 DL-proto-quercitol pentaacetate 
• 72598-62-0 2-bromo-7-oxabicyclo<4.1.0>hept-3-ene 
• 55990-90-4 (1α,2β,3α,5α,7α)-2-Brom-4,8-dioxatricyclo<5.1.0.0^3,5>octan 
• 55990-88-0 (1α,2α,3α,5α,7α)-4,8-Dioxatricyclo<5.1.0.0^3,5>octan-2-ol-acetat 
• 55990-88-0 (1α,2β,3α,5α,7α)-4,8-Dioxatricyclo<5.1.0.0^3,5>octan-2-ol-acetat 
• 18376-41-5 DL-gala-quercitol pentaacetate 
• 608-80-0 benzenehexol 
• 527-22-0 6c-amino-cyclohexane-1r,2t,3c,4t,5c-pentaol 
• 18376-41-5 penta-O-acetyl-DL-1-deoxy-myo-inositol 
• 81562-21-2 DL-1,2:3,4-di-O-cyclohexylidene-6-O-methylthiomethyl-epi-inositol 

Downstream Products

• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 22144-52-1 (+/-)-3r,4t,5c-trihydroxy-cyclohexane-1,2-dione-bis-phenylhydrazone 
• 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 

Relevant academic research and scientific papers

Total synthesis of quercitols: (+)- allo -, (-)- proto -, (+)- talo -, (-)- gala -, (+)- gala -, neo -, and (-)- epi -quercitol

The cyclohexenenones exo- and endo-2 were converted into the cyclohexenyl acetates exo- and endo-3 and exo- and endo-5 with a diastereoselectivity of >99:1 (2 steps). Ether cleavage with DDQ in CH2Cl2/H2O (20:1) and in situ ketal hydrolysis afforded the cyclohexenones 6 and 7 in up to 83% and 87% yield, respectively. Compound 6 was converted into (+)-allo- and (-)-proto-quercitol with a diastereoselectivity of 100:0 (4 steps). Moreover, 6 was carried on to (-)-talo-quercitol whereas 7 furnished the four remaining title quercitols (3-5 steps) including both enantiomers of gala-quercitol.

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

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

Synthesis of the enantiomers of 6-deoxy-myo-inositol 1,3,4,5-Tetrakisphosphate, structural analogues of myo-inositol 1,3,4,5-Tetrakisphosphate

D-myo-Inositol 1,3,4,5-tetrakisphosphate [Ins(1,3,4,5)P4] is produced rapidly from the established second messenger D-myo-inositol 1,4,5trisphosphate [Ins(1,4,5)P4] in stimulated cells. Despite extensive investigations, in particular

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.

A Stereocontrolled Synthesis of proto-Quercitol

Conduritol A tetramethyl ether (2) has been converted by hydroboration-oxidation into proto-quercitol tetramethyl ether (5) which on demethylation afforded a mixture (2:1) of proto-quercitol (4) and vibo-quercitol (11). proto-Quecitol was also obtained (15percent) from conduritol A tetrabenzoate (3) by a similar sequence.