139640-08-7

Upstream product

• 87-89-8 D-myo-inositol 
• 14602-86-9 (1R,2S,5R)-menthyl chloroformate 
• 130296-29-6 Hexakis-O-(dimethylboryl)myo-inositol 
• 41545-19-1 (+)-1,2:5,6-di-O-cyclohexylidene-myo-inositol 
• 153996-48-6 2,3:4,5-di-O-cyclohexylidene-1-O-(1R)-menthyloxycarbonyl-D-myo-inositol 

Downstream Products

• 139640-11-2 Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 22006-88-8 1,4-di-O-methyl-D-myo-inositol 
• 153996-50-0 1D-1-O-2,3,4,5,6-(pentakis)methoxymethylene-myo-inositol 
• 153996-48-6 2,3:4,5-di-O-cyclohexylidene-1-O-(1R)-menthyloxycarbonyl-D-myo-inositol 
• 139640-10-1 1-O-menthoxycarbonyl-2,3:5,6-di-O-isopropylidene-myo-inositol 
• 139640-09-8 1-O-menthoxycarbonyl-2,3:4,5-di-O-isopropylidene-myo-inositol 
• 153996-49-7 Carbonic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis-methoxymethoxy-cyclohexyl ester 

Relevant academic research and scientific papers

Regioselective functionalization of unprotected myo-inositol by electrophilic substitution

Unprotected myo-inositol was treated with various electrophiles, such as aroyl chlorides, tosyl chloride and tert-butyldiphenylsilyl chloride in a solution of LiCl/DMA or DMSO to afford regioselectively 1,3-di-O-substituted or racemic 1-O-substituted deri

Synthesis of D-erythro-ceramide-1-phosphoinositol and its aminoglucosylated derivative - Intermediates in GPI-anchor biosynthesis

The readily available 2,3:4,5-di-O-cyclohexylidene-D-myo-inositol derivative 3 was converted into the 1-O-unprotected D-myo-inositol derivative 6. Reaction with the phosphite derivative 7 of 3-O-tert-butyldimethylsilyl-protected ceramide furnished the target molecule D-erythro-ceramide-1-phosphoinositol (1). Reaction of O-(3,4,6-tri-O-acetyl-2-azido-β-D-glucopyranosyl)trichloroacetimidate (20) with 3 gave exclusively α(1→6)-connected glycoside 21 which was converted into the 1α-O-unprotected derivative 24. Reaction with the D-erythro-azidophytosphingosine-derived ceramide-1-phosphite derivative 17 led, after oxidation and removal of the cyanoethyl group, to protected 2-azido-D-glucopyranosyl-α(1→6)-D-myo-inositol-1-phospho-ceramide (25) which could bo fully deprotected in two steps to afford the target molecule, the ceramide derivative of 2-amino-2-deoxy-D-glucopyranosyl-α(1→6)-D-myo-inositol-1-phosphate (2).

Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol

3-O-Silyl-protected azidosphingosine 3, readily available from D-erythro-azidosphingosine, is transformed into ceramidyl phosphite derivative 5 which is a versatile building block for the synthesis of ceramide-1-O-phosphate and derivatives. This is exhibited for the synthesis of the title compounds 1 and 2.

The regioselective synthesis of enantiomerically pure myo-inositol derivatives. Efficient synthesis of myo-inositol 1,4,5-trisphosphate

Regioselective 1-O-acylation of myo-inositol and simultaneous optical resolution has been achieved by perborylation, transmetallation using di-n-butyltin-bis-acetylacetonate and then acylation with (-)-menthyl chloroformate. Diastereomerically pure 1-O-(-