62076-18-0

Basic information

• Product Name: 1-Deoxyinositol
• Synonyms: 1-Deoxyinositol;1,2,3,4,5-Cyclohexanepentol;Quercite
• CAS NO: 62076-18-0
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.15648
• Mol File: 62076-18-0.mol

Chemical Properties

• Melting Point: 180-181 °C
• Boiling Point: 293.6±40.0 °C(Predicted)
• Appearance: /
• Density: 1.796±0.06 g/cm3(Predicted)
• PKA: 13.42±0.70(Predicted)
• CAS DataBase Reference: 1-Deoxyinositol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Deoxyinositol(62076-18-0)
• EPA Substance Registry System: 1-Deoxyinositol(62076-18-0)

Safety Data

• Hazardous Substances Data: 62076-18-0(Hazardous Substances Data)

Upstream product

• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 65173-65-1 (3aR,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo-1,3-dioxole 
• 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 
• 18376-41-5 DL-proto-quercitol pentaacetate 
• 72598-62-0 2-bromo-7-oxabicyclo<4.1.0>hept-3-ene 
• 55990-88-0 (1α,2α,3α,5α,7α)-4,8-Dioxatricyclo<5.1.0.0^3,5>octan-2-ol-acetat 
• 55990-90-4 (1α,2α,3α,5α,7α)-2-Brom-4,8-dioxatricyclo<5.1.0.0^3,5>octan 
• 86632-82-8 3α,4β,5β,6α-tetramethoxycyclohex-4-ene-1α,2α-diol 
• 18376-41-5 DL-gala-quercitol pentaacetate 
• 1165952-92-0 cyclohexa-1,4-diene 
• 608-80-0 benzenehexol 
• 130633-22-6 (3aα,4α,5β,7β,7aα)-hexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4,5,7-triol 

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 
• 22144-52-1 (+/-)-3r,4t,5c-trihydroxy-cyclohexane-1,2-dione-bis-phenylhydrazone 
• 2975-92-0 (+/-)-1L-cyclohexane-1,3/2,4-tetrol 
• 6216-28-0 DL-(1,3,5/2,4)-1-Acetamido-2,3,4,5-tetra-O-acetylcyclohexanetetrol 
• 20021-56-1 DL-(1,3/2,4)-1,2,3,4-Tetra-O-acetylcyclohexanetetrol 

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

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

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 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 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.

Optically active phenoxypropionic esters

Optically active compounds of the formula I STR1 where R is C1 -C12 -alkyl or -perfluoroalkyl in which one or two non-adjacent CH2 or CF2 groups can also be replaced by --O-- and/or --CO-- and/or --CO--O-- and/or --CH=CH-- and/or --CH-halogen-- and/or --CHCN-- and/or --0--CO--CH-halogen-- and/or --O--CO--CHCN--, or is C1 -C12 -alkyl which can have a terminal chemically reactive group and in which a CH2 group can be replaced by --O--, A1 and A2 are each, independently of one another, 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl and/or Br atoms and/or CH3 groups and/or CN groups and in which one or two CH groups can also be replaced by N, 1,4-cyclohexylene in which one or two non-adjacent CH2 groups can also be replaced by --O-- and/or --S--, 1,4-piperidinediyl, 1,4-bicyclo[2.2.2]octylene, 2,6-naphthalenediyl, decahydro-2,6-naphthalenediyl or 1,2,3,4-tetrahydro-2,6-naphthalenediyl, A3 is unsubstituted or substituted phenyl, Z is --CO--O--, --O--CO--, --CH2 CH2 --, --OCH2 --, --CH2 O--, --C C-- or a single bond and m is 0, 1, 2 or 3.

MICROBIAL OXIDATION IN SYNTHESIS: PREPARATION OF MYO-INOSITOL PHOSPHATES AND RELATED CYCLITOL DERIVATIVES FROM BENZENE.

Pseudomonas putida oxidation of benzene affords cis-3,5-cyclohexadiene-1,2-diol (2) which is used as a novel precursor for the synthesis of D- and L-myo-inositol 1,4,5-triphosphates, (-)-(1) and (+)-(1).The versatility of this approach to functionalised cyclitols is illustrated in the synthesis of myo-inositol 1-phosphate (19), 6-deoxy, 6-deoxy-6-fluoro, and 6-deoxy-6-methyl myo-inositols (31), (37) and (43), and their 1,4,5-trisphosphate derivatives (33), (39) and (45).

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.

Polyfunctionalised Cyclohexanes from Dianhydrodeoxyinositols. cis-Deoxy-1,3(1,4)-inosadiamines from Benzene

A ca. 9 : 1 mixture (yield 87 - 90percent) of the stereoisomeric (1α,2α,6α)-/(1α,2β,6α)-2-bromo-7-oxa-bicyclohept-3-enes (7a/8a) is obtained via controlled NBS bromination of 4,5-epoxycyclohexene (5). 7a/8a are quantitatively equilibrated in the presence of tetraalkylammonium bromides (the equilibrium being controlled by the polarity of the solvent (3 : 7 in acetonitrile) and are isolated pure by chromatography.Through selective halogen substitution (7b/8b, 9b - d/10b - d) and ammonolysis the allylic epoxy alcohols 9a/10a are obtained in high yields.Stereospecific epoxidation of 7a/8a yields the (1α,2α,3α,5α,7α)-/(1α,2β,3α,5α,7α)-diepoxy bromides 12a/14a.The latter are equilibrated quantitatively to mixtures favoring either one in the ratio of ca. 9 : 1 (CCl4) and 1 : 9 (CH3CN), respectively.Upon SN2 substitution with ammonium acylates (-> 13b, c/15b, c) and ammonolysis the naturally not occurring dianhydrodeoxyinositols 13a/15a are isolated in practically quantitative yields.The usefulness of 13a/15a and of various derivatives for the stereoselective synthesis of cis-1,4- and cis-1,3-disubstituted cyclohexanetriols is exemplified by reactions with monovalent (H2O, HI, NaN3) and divalent nucleophiles (NH2NH2, CH3NHNH2).I.a. the cis-deoxy-1,3-inosadiamines 1 (2-deoxystreptamine)/2 and the cis-deoxy-1,4-inosadiamines 3/4 become available in high yields.