652979-99-2

Upstream product

• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 652979-97-0 1,3-O-benzylidene-2-C-methyl-D-erythritol 
• 100-52-7 benzaldehyde 
• 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 
• 80924-06-7 1,3-O-benzylidene D-arabitol 
• 81577-58-4 1,3-(R)-O-benzylidene-D-threitol 
• 99274-32-5 2,4-O-benzylidene-D-threose 

Downstream Products

• 652980-00-2 1,3-O-benzylidene-2-C-methyl-D-erythritol 2,4-bis(phosphoric acid monoester) 

Relevant academic research and scientific papers

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.

Synthesis of Enantiopure 2-C-Methyl-D-erythritol 4-Phosphate and 2,4-Cyclodiphosphate from D-Arabitol

(Equation presented) Two key intermediates of the newly discovered mevalonate-independent pathway for isoprenoid biosynthesis were prepared. Optically pure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate were chemically synthesized from D-arabitol using a convenient benzylidene and tert-butyldimethylsilyl protection of polyhydroxylated intermediates. The new scheme offers a straightforward route to analogues and labeled forms.