129210-15-7

Basic information

• Product Name: 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate
• Synonyms: 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate
• CAS NO: 129210-15-7
• Molecular Weight: 421.295
• Mol File: 129210-15-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate(129210-15-7)
• EPA Substance Registry System: 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate(129210-15-7)

Safety Data

• Hazardous Substances Data: 129210-15-7(Hazardous Substances Data)

Upstream product

• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 158215-59-9 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol 
• 158215-60-2 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-D-myo-inositol 
• 157896-03-2 6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 135131-58-7 1-O-Allyl-2,3,4-tri-O-benzyl-5-O-(p-methoxybenzyl)-D-chiro-inositol 
• 135267-02-6 2-O-Allyl-3,4,5-tri-O-benzyl-6-O-(p-methoxybenzyl)-myo-inositol 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 
• 102997-58-0 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 
• 133076-40-1 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate 
• 135131-60-1 (2R,3R,4R,5S,6R)-2-Allyloxy-3,4,5-tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexanone 
• 135267-00-4 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol 

Downstream Products

• 140391-24-8 6-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1,2-(Cyclic)phosphate 

Relevant articles and documents

Synthesis and characterization of an insulin-mimetic disaccharide

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Synthesis of part of a proposed insulin second messenger glycosylinositol phosphate and the inner core of glycosylphosphatidylinositol anchors

Synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate, an inner core structure found in various glycosylphosphatidylinositols, and the corresponding 1,2-cyclic phosphate, proposed as part of an insulin second messenger glycosylinositol phosphate, is described. Chirality in the inositol part of the molecule was achieved by the use of a known D-camphor acetal intermediate. The glycosylation used 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride as glycosyl donor. The allyl group can be chemoselectively removed, opening a route to oligosaccharides bound to the 4-position of the glucosamine unit. The phosphorylation was accomplished by the phosphoramidate procedure.

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.