652979-98-1

Basic information

• Product Name: Phosphoric acid, [(2S,4R,5S)-5-hydroxy-5-methyl-2-phenyl-1,3-dioxan-4-yl]methyl bis(phenylmethyl) ester
• CAS NO: 652979-98-1
• Molecular Formula: C26H29O7P
• Molecular Weight: 484.486
• Mol File: 652979-98-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Phosphoric acid, [(2S,4R,5S)-5-hydroxy-5-methyl-2-phenyl-1,3-dioxan-4-yl]methyl bis(phenylmethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid, [(2S,4R,5S)-5-hydroxy-5-methyl-2-phenyl-1,3-dioxan-4-yl]methyl bis(phenylmethyl) ester(652979-98-1)
• EPA Substance Registry System: Phosphoric acid, [(2S,4R,5S)-5-hydroxy-5-methyl-2-phenyl-1,3-dioxan-4-yl]methyl bis(phenylmethyl) ester(652979-98-1)

Safety Data

• Hazardous Substances Data: 652979-98-1(Hazardous Substances Data)

Upstream product

• 538-37-4 dibenzyl phosphochloridate 
• 652979-97-0 1,3-O-benzylidene-2-C-methyl-D-erythritol 
• 81577-58-4 1,3-(R)-O-benzylidene-D-threitol 
• 652979-96-9 1,3-O-benzylidene-2-C-methyl-D-erythritol 4-(t-butyldimethylsilyl) ether 
• 652979-92-5 1,3-O-benzylidene-D-threitol 4-(t-butyldimethylsilyl) ether 
• 652979-94-7 1,3-O-benzylidene-D-erythrulose 4-(t-butyldimethylsilyl) ether 
• 99274-32-5 2,4-O-benzylidene-D-threose 
• 80924-06-7 1,3-O-benzylidene D-arabitol 
• 100-52-7 benzaldehyde 

Relevant articles and documents

The dioxanone approach to (2S,3R)-2-C-methylerythritol 4-phosphate and 2,4-cyclodiphosphate, and various MEP analogues

(Chemical Equation Presented) Efficient syntheses of the non-mevalonate pathway intermediates 2-C-methylerythritol 4-phosphate (MEP) and 2-C-methylerythritol 2,4-cyclodiphosphate (ME-2,4-cycloPP), as well as the parent tetrol 2-C-methylerythritol, in enantiopure form from (2S,4R)-cis-2-phenyl-4-tert-butyldimethylsilyloxy-1,3-dioxan-5-one are reported. The 2S configuration of the C-methyl group was installed by highly axial-face selective addition of CH3MgBr (20:1) to the chiral dioxanone carbonyl group. Primary selective monophosphorylation and 2,4-bis-phosphorylation, followed by desilation and hydrogenolysis to the free mono-and diphosphates, and, in the latter case, cyclization to form the eight-membered phosphoryl anhydride, afforded MEP and ME-2,4-cycloPP in good yields. The C2 epimeric analogues, 2-C-methylthreitol and its 4-phosphate, were accessed by LiAlH 4 reduction of the cis,cis epoxide of (2S,4R)-4-tert- butyldimethylsilyloxymethyl-5-methylene-2-phenyl-1,3-dioxane, primary-selective phosphorylation, and cleavage of the silyl, benzylidene, and benzyl protecting groups. Regioselective cleavage of the acetal ring of 1,3-benzylidene 2-C-methylerythritol silyl ether by ozonolysis afforded a 1,2,3-triol 3-monobenzoate intermediate that was converted to the novel amino sugar, 1-amino-1-deoxy-2-C-methylerythritol.