99260-73-8

Usage

InChI:InChI=1/C30H50N10O9/c1-16-21(39-30(46)40-26-22(38-29(34)45)24(43)19(41)15-47-26)25(44)23(37-28(32)33)27(48-16)49-18-8-5-17(6-9-18)7-10-20(42)36-14-4-13-35-12-3-2-11-31/h5-10,16,19,21-27,35,41,43-44H,2-4,11-15,31H2,1H3,(H,36,42)(H4,32,33,37)(H3,34,38,45)(H2,39,40,46)/b10-7+

Upstream product

• 864875-54-7 C₆₁H₉₀N₁₀O₂₀ 
• 864875-53-6 C₆₃H₉₀Cl₃N₉O₂₁ 
• 864875-46-7 (2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4-diol 
• 864875-47-8 (2S,3R,4R,5R,6R)-5-azido-2-(iodomethyl)-6-phenoxytetrahydro-2H-pyran-3,4-diol 
• 68733-19-7 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl acetate 
• 864875-52-5 (2R,3R,4R,5R,6R)-3-azido-5-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-2-methyltetrahydro-2H-pyran-4-yl benzoate 
• 864875-51-4 (2R,3R,4R,5S,6R)-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-4-yl benzoate 
• 864875-35-4 (2R,3R,4S,5R,6R)-3-amino-5-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-2-methyltetrahydro-2H-pyran-4-yl benzoate 
• 864875-50-3 (2R,3R,4R,5S,6R)-2-(4-((E)-10-(tert-butoxycarbonyl)-2,2-dimethyl-4,15-dioxo-3-oxa-5,10,14-triazaheptadec-16-en-17-yl)phenoxy)-5-hydroxy-6-methyl-3-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-4-yl benzoate 
• 864875-37-6 (2R,3S,4R,5R,6R)-3-hydroxy-6-(4-iodophenoxy)-2-methyl-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-4-yl benzoate 
• 864875-49-0 (2R,3S,4R,5R,6R)-3-hydroxy-2-methyl-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-4-yl benzoate 
• 864875-56-9 ((2R,3R,4R,5R,6R)-5-azido-3,4-dihydroxy-6-phenoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 
• 1053711-03-7 Acetic acid (2R,3R,4R,5R)-5-acetoxy-2-isocyanato-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 
• 864875-45-6 (3R,4R,5R,6R)-6-formamido-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate 

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.

Total synthesis of glycocinnasperimicin D

(Chemical Equation Presented) A three-fragment coupling strategy afforded the antibiotic glycocinnasperimicin D (1). The convergent total synthesis features a Heck reaction to form the cinnamoyl glycoside, the [3,3] sigmatropic rearrangement of an allyl c