135267-00-4

Basic information

• Product Name: 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol
• Synonyms: 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol
• CAS NO: 135267-00-4
• Molecular Weight: 490.596
• Mol File: 135267-00-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol(135267-00-4)
• EPA Substance Registry System: 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol(135267-00-4)

Safety Data

• Hazardous Substances Data: 135267-00-4(Hazardous Substances Data)

Upstream product

• 131147-11-0 (±)-2,3-O-isopropylidene-1,5,6-tri-O-benzyl-4-O-allyl-myo-inositol 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 
• 107-18-6 allyl alcohol 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 58706-24-4 (±)-3-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 131146-87-7 (±)-4-O-allyl-1-O-benzyl-2,3;5,6-di-O-isopropylidene-myo-inositol 
• 131146-88-8 (±)-4-O-allyl-1-O-benzyl-2,3-O-isopropylidene-myo-inositol 
• 100-39-0 benzyl bromide 
• 129879-49-8 6-O-allyl-3-O-benzyl-1,2:4,5-di-O-cyclohexylidene-myo-inositol 
• 136282-32-1 6-O-allyl-3-O-benzyl-1,2-O-cyclohexylidene-myo-inositol 
• 23393-20-6 (+/-)-3-O-benzyl-1,2:4,5-di-O,O-cyclohexylidene-myo-inositol 
• 34361-60-9 1,2:4,5-dicyclohexylidene-myo-inositol 
• 87-89-8 D-myo-inositol 

Downstream Products

• 131146-92-4 (+/-)-1,5,6-tri-O-benzyl-4-O-(prop-1-enyl)-myo-inositol 
• 131146-93-5 (+/-)-1,5,6-tri-O-benzyl-myo-inositol 
• 484-68-4 bornesitol 
• 135131-59-8 (2R,3R,4R,5S,6R)-2-Allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexanone 
• 135131-60-1 (2R,3R,4R,5S,6R)-2-Allyloxy-3,4,5-tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexanone 
• 135267-02-6 2-O-Allyl-3,4,5-tri-O-benzyl-6-O-(p-methoxybenzyl)-myo-inositol 
• 158340-85-3 1,2,3,4,5-Penta-O-benzyl-D-chiro-inositol 
• 129210-15-7 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate 
• 158215-60-2 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-D-myo-inositol 
• 158215-59-9 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol 
• 158215-57-7 1-(6-O-Acetyl-2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol 
• 158215-56-6 1-(6-O-Acetyl-2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol 
• 158215-62-4 3,4,5-Tri-O-benzyl-1-O-(dibenzylphosphono)-6-(2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-D-myo-inositol 
• 1053733-28-0 Phosphoric acid (1R,2R,3R,4R,5S,6R)-2-allyloxy-6-((2R,3R,4R,5S,6R)-3-azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-cyclohexyl ester dibenzyl ester 

Relevant articles and documents

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics

Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

Synthesis of racemic 3-methylphosphonate analogues of myo-inositol 3,4-bis- and 1,3,4-trisphosphate

The partially benzyl protected myo-inositol derivatives 11a and 11b, the C-4 and C-1,4 hydroxyl function(s) of which are protected with temporary trans-prop-1-enyl protecting group(s), were readily converted into the respective title compounds 18a and 18b by sequential methylphosphonylation, mild cleavage of the trans-prop-1-enyl group(s), phosphorylation and removal of all permanent benzyl protecting groups.