40617-62-7

Upstream product

• 65173-65-1 (3aR,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo-1,3-dioxole 
• 1165952-92-0 cyclohexa-1,4-diene 
• 406682-04-0 cis-cyclohex-4-ene-1,2-diol 
• 55990-89-1 (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-1,2,3,4,5-cyclohexane-pentol 
• 62776-30-1 1,2:4,5-cis-Dianhydrodesoxyinosit 
• 125477-54-5 conduritol A terabenzoate 
• 130824-35-0 proto-quercitol tetramethyl ether 
• 18376-41-5 DL-proto-quercitol pentaacetate 
• 55990-90-4 (1α,2α,3α,5α,7α)-2-Brom-4,8-dioxatricyclo<5.1.0.0^3,5>octan 
• 62774-78-1 (1α,2α,6α)-2-(2,4-Dinitrophenoxy)-7-oxabicyclo<4.1.0>hept-3-en 
• 863224-36-6 (-)-penta-O-acetyl-2-deoxy-allo-inositol 
• 866334-23-8 C₁₅H₂₆O₇ 
• 866334-21-6 C₁₆H₂₂O₆ 
• 281667-70-7 (1S,6R)-6-(benzyloxy)-3-cyclohexen-1-ol 

Downstream Products

• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 18376-41-5 rac-(1R,2S,3R,4S,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 
• 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 
• 22144-52-1 (+/-)-3r,4t,5c-trihydroxy-cyclohexane-1,2-dione-bis-phenylhydrazone 
• 863224-36-6 (-)-penta-O-acetyl-2-deoxy-allo-inositol 

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

Stereoselective syntheses of (+)-proto, (-)-gala quercitols and carba-l-rhamnose from d-(-)-quinic acid

Efficient syntheses of (+)-proto, (-)-gala quercitols and carba-l-rhamnose from d-(-)-quinic acid are described.

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

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

Synthetic research on cyclitols using C6-chiron, 6-(benzyloxy)-3- cyclohexen-1-ol: A concise and highly diastereoselective synthesis of (-)- gala-quercitol

Transformation of a C6-chiron, 6-(benzyloxy)-3-cyclohexen-1-ol into polyoxygenated cyclohexanes involving a stereodivergen epoxide rearrangement was investigated. An asymmetric synthesis of (-)-gala-quercitol was accomplished via sequential highly diastereoselective epoxidation, base- promoted epoxide rearrangement, and dihydroxylation.

Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics

Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.

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%.