214068-06-1

Upstream product

• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 209050-74-8 (1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol 
• 209050-72-6 Acetic acid (1R,2R,3S,4R,5S)-4-benzyloxy-2-hydroxy-3,5-bis-(4-methoxy-benzyloxy)-6-oxo-cyclohexyl ester 
• 209050-69-1 [(2R,3R,4S,5R,6S)-4-Benzyloxy-6-methoxy-3,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol 
• 1020084-39-2 (2R,3R,4S,5R,6S)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol 
• 209050-68-0 (4aR,6S,7R,8S,8aR)-8-Benzyloxy-6-methoxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 

Relevant academic research and scientific papers

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.

Synthesis of L-α-phosphatidyl-D-myo-inositoi 5-phosphate and L-α- phosphatidyl-D-myo-inositol 3,5-bisphosphate

Two new 5-phosphorylated phosphatidylinositols have been synthesized from methyl α-D-glucopyranoside as the chiral precursor. These new PtdInsP(n)s have been recently detected in mammalian cells.