56981-18-1

Upstream product

• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 
• 75-15-0 carbon disulfide 
• 19465-06-6 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside 
• 74-88-4 methyl iodide 
• 130061-59-5 Methyl 4,6-O-benzylidene-2-deoxy-2-methyl-α-D-glucopyranoside 

Downstream Products

• 68880-92-2 methyl 2,3-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside 
• 135065-92-8 Chloro-acetic acid (2R,3S,5S,6S)-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 135066-03-4 methyl 4-O-bromoacetyl-2,3-dideoxy-2-C-methyl-6-O-triphenylmethyl-α-D-arabino-hexopyranoside 
• 135065-91-7 methyl 2,3-dideoxy-4-O-(diethyl phosponoacetyl)-2-C-methyl-6-O-triphenyl-α-D-arabino-hexo-pyranoside 
• 93381-10-3 methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexo pyranoside 
• 129991-98-6 (2S,3R,5S,6R)-2,5-Dimethoxy-3-methyl-6-trityloxymethyl-tetrahydro-pyran 
• 68880-92-2 (2R,3S,5R,6S)-6-Methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran-3-ol 
• 105930-42-5 (2R,4aR,6S,7R,8aS)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 

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.

Studies directed towards the synthesis of immunosuppressive agent FK-506: Construction of the tricarbonyl moiety

Alkylation of a suitably functionalised dithiane precursor with L-N-(α-haloacetyl)-pipecolic acid methyl ester, followed by oxidation of the active methylene group provided an easy route to 1,2,3-tricarbonyl functionality of FK-506.