135066-03-4

Upstream product

• 19465-06-6 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 
• 56981-18-1 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3.O-<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside 
• 93381-10-3 methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside 
• 68880-91-1 methyl 2,3-dideoxy-2-C-methyl-α-D-arabino-hexopyranoside 
• 68880-92-2 methyl 2,3-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 135065-92-8 Chloro-acetic acid (2R,3S,5S,6S)-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 135065-91-7 methyl 2,3-dideoxy-4-O-(diethyl phosponoacetyl)-2-C-methyl-6-O-triphenyl-α-D-arabino-hexo-pyranoside 

Relevant academic research and scientific papers

Introduction of a chiral centre on C-6 of a carbohydrate unit: Application to the synthesis of the C-2 to C-15 fragment of ionomycin

Glucose is converted into the α,β-unsaturated urono-8,4-lactone 29 using an intramolecular Wadsworth-Emmons reaction. Higher order cuprates add to the lactone to provide the C-6 substituted carbohydrate derivative with high stereoselectivity. This product can be converted into the dithiane 34b which when coupled with an appropriate epoxide yields compound 37 which contains the C-2 to C-15 fragment of ionomycin with the correct absolute stereochemistry at each asymmetric centre for conversion into ionomycin.