26671-58-9

Basic information

• Product Name: 5-deoxyinositol
• Synonyms: 5-deoxyinositol;5-Deoxy-L-neo-inositol;5-Deoxy-myo-inositol;neo-Quercitol
• CAS NO: 26671-58-9
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.15648
• Mol File: 26671-58-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 293.6°Cat760mmHg
• Flash Point: 146.2°C
• Appearance: /
• Density: 1.796g/cm³
• Vapor Pressure: 0.00018mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: 5-deoxyinositol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-deoxyinositol(26671-58-9)
• EPA Substance Registry System: 5-deoxyinositol(26671-58-9)

Safety Data

• Hazardous Substances Data: 26671-58-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H12O5/c7-2-1-3(8)5(10)6(11)4(2)9/h2-11H,1H2/t2-,3+,4+,5-,6?

Upstream product

• 62776-30-1 1,2:4,5-cis-Dianhydrodesoxyinosit 
• 20097-43-2 2-amino-2-deoxy-neo-isonitol hexa-acetate 
• 68907-51-7 rac-(1R,2S,3S,4R,5S)-cyclohexane 1,2,3,4,5-pentaylpentaacetate 
• 72598-62-0 2-bromo-7-oxabicyclo<4.1.0>hept-3-ene 
• 55990-90-4 (1α,2α,3α,5α,7α)-2-Brom-4,8-dioxatricyclo<5.1.0.0^3,5>octan 
• 55990-88-0 (1α,2β,3α,5α,7α)-4,8-Dioxatricyclo<5.1.0.0^3,5>octan-2-ol-acetat 
• 1201502-40-0 1,3,5-tri-O-benzyl-2-deoxy-neo-inositol 
• 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 
• 1165952-92-0 cyclohexa-1,4-diene 
• 406682-04-0 cis-cyclohex-4-ene-1,2-diol 

Downstream Products

• 527-42-4 1-deoxy-scyllo-inositol 
• 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 
• 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

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.

Intramolecular hydrogen abstraction in radicals derived from inositol 1,3-acetals: Efficient access to cyclitols

The benzylidene acetals obtained by cleavage of the orthobenzoate moiety in myoinositol 1,3,5-orthobenzoate were used to prepare mono- as well as di-deoxy inositol derivatives via their xanthates. The dideoxygenation is a result of intramolecular abstraction of the benzylidene acetal hydrogen and subsequent cleavage of the acetal ring. Such a cleavage does not take place in analogous acetals derived from, other orthoesters. The 1, 3-acetals derived from, myo- inositol 1,3,5-orthoesters were also used to prepare neo-inositol and isomeric deoxy-amino inositols. Most of the reactions in these synthetic sequences starting from myo-inositol give one product in each step. The results presented here show that myo-inositol 1,3,5-orthobenzoate offers many advantages over other orthoesters for the synthesis of cyclitol derivatives from myo-inositol.

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