402832-38-6

Basic information

• Product Name: L-1-O-benzyl-2-O-methyl-chiro-inositol
• Synonyms: L-1-O-benzyl-2-O-methyl-chiro-inositol
• CAS NO: 402832-38-6
• Molecular Weight: 284.309
• Mol File: 402832-38-6.mol

Chemical Properties

• CAS DataBase Reference: L-1-O-benzyl-2-O-methyl-chiro-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: L-1-O-benzyl-2-O-methyl-chiro-inositol(402832-38-6)
• EPA Substance Registry System: L-1-O-benzyl-2-O-methyl-chiro-inositol(402832-38-6)

Safety Data

• Hazardous Substances Data: 402832-38-6(Hazardous Substances Data)

Upstream product

• 642-38-6 quebrachitol 
• 157727-65-6 1-O-benzoyl-3,4:5,6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol 
• 6848-53-9 L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol 

Downstream Products

• 402724-04-3 L-4-O-benzyl-3-O-1,2-O-(2,2,2-trichloroethylidene)-3-O-cyclohexylcarbamoyl-5-O-methyl-muco-inositol 
• 402724-06-5 L-1-O-benzyl-6-O-cyclohexylcarbamoyl-3-O-formyl-2-O-methyl-4,5-O-trichloroethylidene-muco-inositol 
• 404351-01-5 D-2-O-benzyl-3-O-cyclohexylcarbamoyl-4-(N,N'-dicyclohexylureido)-4-deoxy-1-O-methyl-5,6-O-trichloroethylidene-chiro-inositol 

Relevant articles and documents

Enzyme-catalysed synthesis of galactosylated 1D- and 1L-chiro-inositol, 1D-pinitol, myo-inositol and selected derivatives using the β-galactosidase from the thermophile Thermoanaerobacter sp. strain TP6-B1

The products from the enzymatic β-D-galactopyranosylation of 1D-chiro-inositol, 1D-pinitol, 1D-3-O-allyl-4-O-methyl-chiro-inositol, 1D-3,4-di-O-methyl-chiro-inositol, 1L-chiro-inositol and myo-inositol in combined yields ranging from 46% to 64% have been

Selective epimerization of L-chiro-inositol to L-muco- and D-chiro-inositol derivatives

In a one step procedure, L-1-O-benzyl-2-O-methyl-chiro-inositol (1) was acetalized to the L-muco-inositol derivatives 2, 3 and D-2-O-benzyl-3-O-cyclohexylcarbamoyl-4-deoxy-4-(N,N'-dicyclohexylureido)-1- O-methyl-5,6-O-trichloroethylidene-chiro-inositol (4). Complete conversion of L-1-O-benzyl-6-O-cyclohexylcarbamoyl-3-O-formyl-2-O-methyl-4,5-O- trichloroethylidene-muco-inositol (3) into L-1-O-benzyl-6-O-cyclohexylcarbamoyl-2-O-methyl-4,5-O-trichloroethylidene- muco-inositol (2) is feasible by deformylation in boiling methanolic triethylamine. Furthermore, stepwise deprotection of 2 and 4 is described. Thus, compounds 5, 10, and 7 were obtained by decarbamoylation of 2, 4, and 6, respectively, with boiling methanolic sodium methoxide. The trichloroethylidene group of L-1-O-benzyl-2-O-methyl-4,5-O-trichloroethylidene-muco-inositol (5) was removed in a two step procedure (hydrodechlorination-deacetalization) via the ethylidene acetal 7 to give L-1-O-benzyl-2-O-methyl-muco-inositol (9). On refluxing D-chiro-inositol derivative 4 with 99% acetic acid, the ureido moiety was cleaved generating D-2-O-benzyl-4-cyclohexylamino-3-O-cyclohexylcarbamoyl-4-deoxy-1-O-methyl-5, 6-O-trichloroethylidene-chiro-inositol (11). By contrast, cleavage of the ureido moiety of 10 was relatively difficult. The corresponding D-2-O-benzyl-4-cyclohexylamino-4-deoxy-1-O-methyl-5,6-O-trichloroethylidene- chiro-inositol (12) was only formed in small amounts. The structures of 1, 3 and 10 were confirmed by X-ray analysis.