52432-16-3

Upstream product

• 6763-52-6 1L-1-O-(p-tolylsulfonyl)-chiro-inositol 
• 273749-59-0 methyl 2-azido-2-deoxy-α/β-D-glucopyranoside 
• 58769-23-6 1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol 
• 1122-84-5 1-ethoxycyclohexene 
• 6763-54-8 1L-1,2:3,4-di-O-cyclohexylidene-5-O-methyl-6-O-(p-tolylsulfonyl)-chiro-inositol 
• 6848-53-9 L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol 
• 639799-14-7 (1S,2R,3R,4S)-2,3,4-tri-O-acetyl-1-azidoconduritol B 
• 639079-41-7 (1S,2R,3R,4S)-1-azidoconduritol B 
• 639079-40-6 (1R,2S,3R,6S)-6-azido-2-bromocyclohex-4-ene-1,3-diol 
• 140696-30-6 (1R,2S,3R,6R)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-ol 
• 169529-92-4 (+)-(1R,2S,3S,4R)-2,3-dibromocyclohex-5-ene-1,4-diol 
• 639079-44-0 (+)-4,5,6-tri-O-acetyl-3-azido-myo-inositol 
• 97169-82-9 1L-1-azido-1-deoxy-2,3:4,5-di-O-isopropylidene-6-O-methyl-myo-inositol 

Downstream Products

• 153212-81-8 D-3-amino-3-deoxy-myo-inositol 1,4,5-trisphosphate 
• 1053263-66-3 D-3-azido-1,4,5-tri-O-benzoyl-6-O-benzyl-3-deoxy-myo-inositol 
• 1054702-95-2 D-3-azido-4,5-di-O-benzoyl-6-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol 
• 56845-76-2 (+)-3-deoxy-3-amino-myo-inositol 
• 97169-48-7 (-)-1,2,4,5,6-penta-O-acetyl-3-deoxy-3-azido-myo-inositol 

Relevant academic research and scientific papers

Ferrier Carbocyclization-Mediated Synthesis of Enantiopure Azido Inositol Analogues

Azide-modified inositol (InoAz) analogues are valuable as inhibitors and have shown promise as metabolic chemical reporters (MCRs) for labeling inositol-containing glycoconjugates in eukaryotic cells and potentially in mycobacteria, but the synthesis of enantiomerically pure InoAz analogues via traditional approaches is challenging. As a complementary route, here we investigated the application of the Ferrier carbocyclization reaction to the synthesis of enantiopure InoAz analogues starting from readily available azido glucosides. Using this approach combined with a para-methoxybenzyl protecting group strategy, 3-azido-3-deoxy- and 4-azido-4-deoxy-d-myo-inositol were efficiently synthesized. 5-Azido-5-deoxy-d-myo-inositol was inaccessible due to an unusual β-elimination reaction, wherein the azide anion acted as the leaving group. The reported strategy is expected to facilitate continued development of synthetic InoAz analogues as inhibitors or MCRs of inositol-containing glycoconjugates in eukaryotic and mycobacterial systems.

Stereoselective synthesis of several azido/amino- and diazido/diamino-myo-inositols and their phosphates from p-benzoquinone

A practical route is described for the preparation of azido-myo-inositols, amino-myo-inositols and azido-conduritol B derivatives. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol B derivative. Selective introduction of nitrogen-containing functional groups in four of the six possible positions in the cyclitol moiety is followed by further functionalization to yield the target compounds.

Synthesis and evaluation of 3-modified 1D-myo-inositols as inhibitors and substrates of phosphatidylinositol synthase and inhibitors of myo-inositol uptake by cells

A number of 3-substituted 1D-myo-inositols were synthesized and evaluated as substrates for phosphatidylinositol synthase and uptake by intact cells. 1D-3-Amino-, -3-chloro-, and -3-(acetylthio)-3-deoxy-myo-inositols were all synthesized by nucleophilic d

Cyclitol Reactions, XII. - Enantioselective Synthesis of the Central Pseudodisaccharide Unit of α-Glycosidase Inhibitors of the Oligostatine Type

A pseudodisaccharide unit of the α-glycosidase inhibitors of the oligostatine type has been synthesized.At first a synthesis of the enantiomeric pure derivative of the branched amino inositol 26 has been developed.A linkage of 26 with the reactive epoxide