147127-66-0

Basic information

• Product Name: 1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris-chiro-inositol
• CAS NO: 147127-66-0
• Molecular Weight: 1008.85
• Mol File: 147127-66-0.mol

Chemical Properties

• CAS DataBase Reference: 1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris-chiro-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris-chiro-inositol(147127-66-0)
• EPA Substance Registry System: 1L-(-)-2,3,5-tri-O-benzyl-1,4,6-tris-chiro-inositol(147127-66-0)

Safety Data

• Hazardous Substances Data: 147127-66-0(Hazardous Substances Data)

Upstream product

• 98906-30-0 (±)-2,3,6-tri-O-benzyl-myo-inositol 
• 102690-88-0 bis(2-cyanoethyl) diisopropylamidophosphite 
• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 
• 98-88-4 benzoyl chloride 
• 127401-30-3 rac-3,6-di-O-benzyl-4,5-di-O-benzoyl-myo-inositol 
• 111446-91-4 (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol 
• 109522-10-3 Diisopropyl-phosphoramidous acid 2-cyano-ethyl ester (1R,2S,3R,4R,5S,6R)-2,3,5-tris-benzyloxy-4,6-bis-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-cyclohexyl ester 
• 136521-84-1 (-)-1L-2,3,5-tri-O-benzyl-chiro-inositol 
• 109522-11-4 Phosphorous acid bis-(2-cyano-ethyl) ester (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester 

Relevant articles and documents

Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications

Membrane-permeant derivatives of inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(Bt3IP3/AM), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (IP3/AM), hexakis(propionyloxymethyl) ester (IP3/PM) and hexakis(butyryloxymethyl) ester (IP3/BM) were therefore synthesized. Whereas extracellular application of up to 200 μM of Bt3IP3/AM or IP3/AM to 1321N1 astrocytoma cells failed to mobilize internal calcium, IP3/PM and IP3/BM released internal calcium at concentrations as low os 20 μM and 2 μM, respectively.

The preparation of phosphorylated intermediates for the synthesis of racemic and chiral myo-inositol 1,4,5-trisphosphate and its phosphorothioate analogues

Reaction of racemic 1,2,4-tri-O-benzyl-myo-inositol 3- with bis(2,2,2-trichloroethyl) phosphorochloridate gave a mixture of the 3,5- and 3,6-bisphosphate derivatives which were difficult to separate and could not be phosphorylated further.The bisphosphates were synthesised by the phosphorylation of the 5- and 6-O-(cis-prop-1-enyl) derivatives of racemic 1,2,4-tri-O-benzyl-myo-inositol and subsequent acidic hydrolysis. 1D-2,3,6-Tri-O-benzyl-1,4-di-O-(cis-prop-1-enyl)-myo-inositol was converted into crystalline 1D-2,3,6-tri-O-benzyl-myo-inositol 1,4-bis(dibenzyl phosphate), and thence into the crystalline 1,4,5-tris(dibenzyl phosphate) which was also obtained, using dibenzyloxy(diisopropylamino)phosphine, from 1D-2,3,6-tri-O-benzyl-myo-inositol.The latter compound was converted, using bis(2-cyanoethoxy)(diisopropylamino)phosphine, into the crystalline 1,4,5-tris which was also obtained from the 4,5-bis.Both the tris and the tris(dibenzyl phosphate) are intermediates suitable for the synthesis of 1,4,5-IP3.

SYNTHESIS OF DL-MYO-INOSITOL 1,4,5-TRISPHOSPHATE

DL-myo-inositol 1,4,5-triphosphate has been synthesised from (+/-) 1,2,4-tri-O-benzyl-myo-inositol using a phosphite chemistry approach.