68907-51-7

Basic information

• Product Name: rac-(1R,2S,3S,4R,5S)-cyclohexane 1,2,3,4,5-pentaylpentaacetate
• Synonyms: rac-(1R,2S,3S,4R,5S)-cyclohexane 1,2,3,4,5-pentaylpentaacetate
• CAS NO: 68907-51-7
• Molecular Weight: 374.345
• Mol File: 68907-51-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: rac-(1R,2S,3S,4R,5S)-cyclohexane 1,2,3,4,5-pentaylpentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: rac-(1R,2S,3S,4R,5S)-cyclohexane 1,2,3,4,5-pentaylpentaacetate(68907-51-7)
• EPA Substance Registry System: rac-(1R,2S,3S,4R,5S)-cyclohexane 1,2,3,4,5-pentaylpentaacetate(68907-51-7)

Safety Data

• Hazardous Substances Data: 68907-51-7(Hazardous Substances Data)

Upstream product

• 4270-96-6 benzenepentol 
• 108-24-7 acetic anhydride 
• 19669-12-6 Acetic acid (1R,2S,3R,4S,5S,6R)-2,3,5,6-tetraacetoxy-4-chloro-cyclohexyl ester 
• 1165952-92-0 cyclohexa-1,4-diene 
• 488-73-3 cyclohexane-1r,2c,3,4t,5t-pentaol 
• 676543-77-4 (1S,2S,5S)-(+)-2,5-bis(acetyloxy)cyclohex-3-en-1-yl acetate 

Downstream Products

• 488-73-3 epi-quercitol 
• 17278-12-5 D-1,3,4/2,5-cyclohexanepentol 
• 26671-58-9 (1α,2β,3β,4β,5α)-1,2,3,4,5-Cyclohexanpentol 
• 488-73-3 cyclohexane-1r,2c,3,4t,5t-pentaol 
• 488-73-3 (+/-)-cyclohexane-1r,2c,3t,4c,5t-pentaol 
• 488-73-3 DL-gala-quercitol 
• 488-73-3 (1α,2β,3α,4α,5β)-1,2,3,4,5-Cyclohexanpentol 

Relevant articles and documents

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.

Highly stereoselective and stereospecific syntheses of a variety of quercitols from d-(-)-quinic acid

The highly stereoselective synthesis of (-)-epi-, (-)-allo- and neo-quercitols as well as stereospecific synthesis of (-)-talo- and (+)-gala-quercitols have been achieved. The general strategy is employing dihydroxylation of the isolated double bond of various kinds of protected chiral (1,4,5)-cyclohex-2-ene-triols, which are derived from d-(-)-quinic acid. The choosing of protecting groups from either BBA (butane 2,3-bisacetal) or acetyl groups will result in the various degrees of stereoselectivity of dihydroxylation. On the other hand, the cyclohexylidene acetal moiety is attributed to the stereospecificity during dihydroxylation to afford the request molecules.

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.