214068-76-5

Upstream product

• 291527-84-9 1-O-(4'-methoxybenzyl)-2,3,4,6-tetra-O-benzyl-myo-inositol-5-(dibenzyl phosphate) 
• 291527-91-8 (-)-2,3,4,6-tetra-O-benzyl-myo-inositol-5-(dibenzyl phosphate) 
• 291527-89-4 Phosphoric acid dibenzyl ester (1S,2R,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4-dihydroxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester 
• 149713-85-9 4,6-di-O-benzyl-myo-inositol 
• 98510-25-9 meso-4,6-di-O-benzyl-D-myo-inositol-1,3,5-O-orthoformate 
• 291527-81-6 Phosphoric acid dibenzyl ester (1S,2S,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-5,6-dihydroxy-cyclohexyl ester 

Relevant academic research and scientific papers

Concise syntheses of L-α-phosphatidyl-D-myo-inositol 3-phosphate (3- PIP), 5-phosphate (5-PIP), and 3,5-bisphosphate (3,5-PIP2)

Highly efficient, asymmetric total syntheses of the title phospholipids as well as short chain and crosslinkable aminoether analogs were achieved in five to seven steps from a readily available myo-inositol derivative. (C) 2000 Elsevier Science Ltd.

Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives

New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsPn derivatives with diacylglyceryl moieties of different chain lengths.