669763-31-9

Upstream product

• 304865-92-7 1,3,4,6-tetra-O-acetyl-2-deoxy-2-methoxycarbonylamino-α,β-D-glucopyranoside 
• 108-95-2 phenol 
• 61566-44-7 (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(methoxycarbonylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate 

Downstream Products

• 669763-33-1 ((2R,3S,4R,5R,6R)-3,4-dihydroxy-5-(methoxycarbonylamino)-6-phenoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 
• 669763-36-4 Acetic acid (2S,3S,4R,5R,6R)-3-acetoxy-2-iodomethyl-5-methoxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester 
• 669763-38-6 Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-methoxycarbonylamino-2-methyl-6-phenoxy-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

Synthesis of glycocinnasperimicin D

The first total synthesis of amino sugar antibiotic glycocinnasperimicin D (1) has been achieved by a convergent, three-component coupling strategy. The key steps involve the Heck-Mizoroki reaction by using the iodophenyl glycoside 50 and acryl amide 32 to furnish the right core structure of 1, and the construction of the urea glycoside employing the reaction of glycosyl isocyanate 8 with amino sugar 9. Glycosyl isocyanate 8 was prepared by the oxidation of isonitrile 10, which displayed excellent reactivity in the coupling event. Synthetic roadblocks, encountered during this synthetic effort, have led to the development of the α-selective, Lewis acid catalyzed phenyl glycosylation process with 2-amino-hexopyranose and a procedure for acetonide deprotection without affecting the silyl ethers.

Glycocinnasperimicin D Synthetic Studies: Synthesis of Cinnamoyl Glycosides via Iodination-Heck Reaction Sequence Starting from Phenyl Glycosides

A new approach for the synthesis of cinnamoyl glycoside has been developed via iodination-Heck reaction sequence starting from phenyl glycoside. Successful application of this procedure accomplished the construction of the right core structure of aminosug