38643-30-0

Upstream product

• 488-58-4 epi-Inositol 
• 38643-29-7 (+/-)-O¹,O²;O³,O⁴;O⁵,O⁶-triisopropylidene-epi-inositol 
• 116-11-0 2-Methoxypropene 
• 87-89-8 D-myo-inositol 
• 77-76-9 2,2-dimethoxy-propane 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 115072-67-8 (3aR,4S,5S,5aR,8aR,8bS)-2,2,7,7-Tetramethyl-4,5-bis-[((E)-propenyl)oxy]-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxole 
• 115072-69-0 5,6-di-O-allyl-1,2:3,4-di-O-isopropylidene-myo-inositol 
• 115072-66-7 (±)-5,6-di-O-benzoyl-1,2:3,4-di-O-isopropylidene-myo-inositol 
• 115072-66-7 (±)-3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 

Downstream Products

• 39248-61-8 (+/-)-O⁶-acetyl-O¹,O²;O³,O⁴-diisopropylidene-O⁵-(toluene-4-sulfonyl)-epi-inositol 
• 122596-73-0 (+/-)-O¹,O²;O³,O⁴-diisopropylidene-O⁵,O⁶-bis-(4-nitro-benzenesulfonyl)-epi-inositol 
• 4782-75-6 conduritol D 
• 65533-41-7 (±)-3-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 139686-87-6 (3aS,4S,5S,5aR,8aS,8bS)-5-Benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-ol 
• 526-87-4 (+/-)-Conduritol F 
• 13035-65-9 (±)-1,6-di-O-benzyl-myo-inositol 
• 165883-86-3 D-3-O-benzoyl-myo-inositol 
• 26326-85-2 Ins(1,2,3,4,6)P5 
• 26326-86-3 Ins(1,2,3,4,5)P₅ 
• 114418-96-1 Ins(1,2,4,5,6)P₅ 

Relevant academic research and scientific papers

H2SO4-silica: An eco-friendly heterogeneous catalyst for the differential protection of myo-inositol hydroxyl groups

There is enormous interest in myo-inositol derivatives as they serve as precursors for the synthesis of several biologically important phosphoinositols, natural products, catalyst, supramolecular architectures etc. However the presence of six secondary hy

(±)-1,2:5,6-Di-O-isopropylidene-myo-inositol and (±)-6-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol: A practical preparation of key intermediates for myo-inositol phosphates

A simple and practical synthetic procedure for the versatile intermediates, (±)-1,2:5,6-di-O-isopropylidene-myo-inositol and (±)-6-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol, is described.

Practical synthesis of all inositol stereoisomers from myo-inositol

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.

A convenient synthesis of D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3) and L-myo-inositol 1,4,5-trisphosphate (Ins(3,5,6)P3)

An efficient synthesis of an optically active inositol derivative that is a precursor to D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3, (-)) is described. Crystallization of the diastereomers of (±) -1-O-[(+)- menthoxycarbonyl]-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol diastereomers from methanol gives only one diastereomer. Alkaline hydrolysis gives the useful inositol derivative (-)-6-O-benzyl-2,3:4,5-di-O- isopropylidene-myo-inositol. Likewise, crystallization of the diastereomers of (±)-3-O-[(-)-menthoxycarbonyl]-4-O-benzyl-1,2:5,6-di-O-isopropylidene- myo-inositol from methanol gave a pure compound which could be hydrolyzed to give (+)-4-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol, a precursor to D-myo-inositol 3,5,6-trisphosphate (Ins(3,5,6)P3, (+)). The ease with which these enantiomerically pure inositol derivatives were isolated may facilitate the synthesis of more complex inositol phosphate derivatives such as D-myo- inositol 1,3,4,5-tetrakisphosphate.

Regioselective functionalizations and conformational studies of di-O-isopropylidene-myo-inositol derivatives

(+/-)-1,2:4,5-Di-O-isopropylidene-myo-inositol (5) and (+/-)-1,2:5,6-di-O-isopropylidene-myo-inositol (6) could be regioselectively functionalized in reactions including alkylation, acylation, and silylation at HO-3 in preference to HO-6 and HO-4, respectively, under specific conditions.The presence of intramolecular hydrogen bonding was evident in IR and 1H NMR spectra, and the HO-3 group was identified as the hydrogen-bonding donor in 5 and 6.In their crystalline states, diol 5 prefers a chair conformation and diol 6 a twist boat (skew) conformation.Both compounds appear to have substantial populations of chair conformations in the gas and solution phases, on the basis of the MM-2 energy minimizations and comparisons of vicinal coupling constants observed in the 1H NMR spectra (in CDCl3 and Me2SO-d6) and calculated from the crystal and MM-2 conformations.It is suggested as an explanation for the observed selectivities that the kinetic acidity of the HO-3 group may be enhanced through its intramolecular hydrogen bonding with the cis-vicinal oxygen, or the nucleophilicity of the 3-alkoxide may be enhanced due to its interaction with the cis-vicinal oxygen in a manner similar to the through-space α-effect.

Improved preparation of acetals of myo-inositol and its (+/-)-1-benzyl ether: conformational analysis of di-O-isopropylidene-myo-inositol derivatives

The acid-catalysed reactions of myo-inositol with 3-5 equiv. of 2-methoxypropene or 2,2-dimethoxypropane in methyl sulfoxide or N,N-dimethylformamide gave mixtures of the 1,2:4,5-, 1,2:5,6-, and 1,2:3,4-di-O-isopropylidene derivatives with little or none

THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE CHEMISTRY. PART 21. (+/-)-1,2:5,6- AND (+/-)-1,2:3,4-DI-O-ISOPROPYLIDENE-MYO-INOSITOL. THE UNUSUAL BEHAVIOUR OF CRYSTALS OF (+/-)-3,4-DI-O-ACETYL-1,2,5,6-TETRA-O-BENZYL-MYO-INOSITO ON HEATING AND COOLING: A '

Racemic 1,2-O-isopropylidene-myo-inositol was converted into a mixture of 1,2:5,6-, 1,2:3,4-, and 1,2:4,5-di-O-isopropylidene-myo-inositols which were resolved by g.l.c.The 1,2:4,5 and 1,2:5,6- isomers were isolated from the mixture as benzoate derivative