10583-42-3

Basic information

• Product Name: 5-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol
• CAS NO: 10583-42-3
• Molecular Weight: 580.721
• Mol File: 10583-42-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 5-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol(10583-42-3)
• EPA Substance Registry System: 5-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol(10583-42-3)

Safety Data

• Hazardous Substances Data: 10583-42-3(Hazardous Substances Data)

Upstream product

• 87-89-8 D-myo-inositol 
• 111392-24-6 C₄₀H₄₄O₆ 
• 39698-23-2 1,2,3,4-tetra-O-benzyl-6-O-prop-1-enyl-myo-inositol 
• 10583-42-3 6-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 111392-24-6 C₄₀H₄₄O₆ 
• 39698-23-2 1,2,3,4-tetra-O-benzyl-5-O-prop-1-enyl-myo-inositol 
• 10583-42-3 5-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 98906-26-4 (3aR,4R,5S,6S,7R,7aS)-5,6-Bis-allyloxy-4,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 98925-52-1 (+/-)-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 58706-20-0 (+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 100-39-0 benzyl bromide 
• 64656-21-9 5,6-di-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol 

Downstream Products

• 10583-42-3 5-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 39698-23-2 1,2,3,4-tetra-O-benzyl-5-O-prop-1-enyl-myo-inositol 
• 111392-24-6 C₄₀H₄₄O₆ 
• 10583-42-3 6-O-allyl-1,2,3,4-tetra-O-benzyl-myo-inositol 
• 39698-23-2 1,2,3,4-tetra-O-benzyl-6-O-prop-1-enyl-myo-inositol 
• 111392-24-6 C₄₀H₄₄O₆ 
• 108235-14-9 D,L-2,3,4,5,6-penta-O-benzyl-myo-inositol 1-(methanesulfonate) 
• 134275-56-2 myo-inositol 1-(-3,4-di-palmitoyloxybutyl)-sulfonate 
• 134275-56-2 myo-inositol 1-(-3,4-di-palmitoyloxybutyl)-sulfonate 
• 134275-53-9 2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethanesulfonic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyl ester 
• 134275-53-9 2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethanesulfonic acid (1S,2S,3R,4S,5S,6S)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyl ester 
• 134275-54-0 3,4-Dihydroxy-butane-1-sulfonic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyl ester 
• 134275-54-0 3,4-Dihydroxy-butane-1-sulfonic acid (1S,2S,3R,4S,5S,6S)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyl ester 
• 134275-55-1 Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyloxysulfonyl)-propyl ester 

Relevant articles and documents

Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation

O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results presented in this article as well as those available in the literature suggests that chelation of metal ions by inositol derivatives plays a significant role in the observed regioselectivity. Steric factors associated with the axial or equatorial disposition of the reacting hydroxyl groups do not contribute much to the outcome of these O-alkylation reactions. These results could serve as guidelines in planning synthetic strategies involving other carbohydrates and their derivatives.

Syntheses of penta-O-benzyl-myo-inositols, O-β-L-arabinosyl-(1 → 2)sn-myo-inositol, O-α-D-galactosyl-(1 → 3)-sn-myo-inositol, and O-α-D-galactosyl-(1 → 6)-O-α-D-galactosyl-(1 → 3)-sn-myo-inositol

Two-step conversions of myo-inositol into (±)-2,3,4,5,6- and 1,3,4,5,6-penta-O-benzyl-myo-inositols are described. Starting from these monohydroxy derivatives of myo-inositol, O-β-L-arabinopyranosyl-(1→2)-sn-myo-inositol from Japanese green tea, Camellia sinensis, and O-α-D-galactopyranosyl-(1→3)-sn-myo-inositol (galactinol) as well as its homolog, O-α-D-galactopyranosyl-(1→6(II))-galactinol, were synthesized by way of the in situ activating glycosylation procedure.

AN APPROACH TOWARD THE SYNTHESIS OF RACEMIC MYO-INOSITOL 1-( 3,4-DI-PALMITOYLOXYBUTYL)-SULFONATE

Substitution of the triflate function in 1,2-isopropylidene-sn-glycerol 3-trifluoromethanesulfonate by the α-lithio-anion of 2,3,4,5,6-penta-O-benzyl-myo-inositol 1-methanesulfonate afforded, after acid hydrolysis of the acetonide function, followed by pa