134756-58-4

Upstream product

• 108-98-5 thiophenol 
• 69534-73-2 3,4,6-O-tri-O-acetyl-D-glucal 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 111425-52-6 thiophenyl 2,3-dideoxy-α-D-glucopyranoside 

Downstream Products

• 63598-38-9 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose 
• 128358-59-8 3-O-benzyl-4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranosyl benzenesulfonamide 
• 1279711-50-0 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1R-deutero-D-altropyranose 
• 5987-33-7 4,6-O-benzylidene-D-allal 
• 183989-04-0 2-Trimethylsilanyl-ethanesulfonic acid {(2R,4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3S,4S)-2-benzyloxymethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-3,4-dihydro-2H-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-amide 
• 183989-00-6 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide 
• 183988-92-3 C₇₃H₉₆N₄O₁₇S₂Si₂ 
• 183988-93-4 C₇₃H₉₆N₄O₁₇S₂Si₂ 
• 134756-68-6 O-<2-benzenesulfonamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-allopyranosyl>-β-(1->4)-6-O-benzyl-2-bromo-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-α-D-altropyranosyl benzenesulfonamide 
• 134756-67-5 O-<2-benzenesulfonamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-allopyranosyl>-β-(1->4)-1,5-anhydro-6-O-benzyl-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose 
• 76513-66-1 1,5-anhydro-4,6-O-benzylidene-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose 
• 134756-60-8 1,5-anhydro-6-O-benzyl-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose 
• 128442-04-6 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose 

Relevant academic research and scientific papers

Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

Glycals and 4-deoxypentenosides (4-DPs), unsaturated pyranosides with similar structures and reactivity profiles, can exhibit a high degree of stereoselectivity upon epoxidation with dimethyldioxirane (DMDO). In most cases, the glycals and their corresponding 4-DP isosteres share the same facioselectivity, implying that the pyran substituents are largely responsible for the stereodirecting effect. Fully substituted dihydropyrans are subject to a "majority rule", in which the epoxidation is directed toward the face opposite to two of the three groups. Removing one of the substituents has a variable effect on the epoxidation outcome, depending on its position and also on the relative stereochemistry of the remaining two groups. Overall, we observe that the greatest loss in facioselectivity for glycals and 4-DPs is caused by removal of the C3 oxygen, followed by the C5/anomeric substituent, and least of all by the C4/C2 oxygen. DFT calculations based on polarized-π frontier molecular orbital (PPFMO) theory support a stereoelectronic role for the oxygen substituents in 4-DP facioselectivity, but less clearly so in the case of glycals. We conclude that the anomeric oxygen in 4-DPs contributes toward a stereoelectronic bias in facioselectivity whereas the C5 alkoxymethyl in glycals imparts a steric bias, which at times can compete with the stereodirecting effects from the other oxygen substituents.

The total synthesis of allosamidin. Expansions of the methodology of azaglycosylation pursuant to the total synthesis of allosamidin. A surprising enantiotopic sense for a lipase-induced deacetylation

Allosamidin, recently isolated from mycelial extracts of Streptomyces sp. 1713, is a powerful and selective chitinase inhibitor. The total synthesis of allosamidin is described herein. The electric eel acetylcholinesterase-mediated enantioselective hydrolysis of (trans,trans)-2-(benzyloxy)cyclopentene-1,3-diol diacetate accessed a monoacetyl derivative. Five additional steps produced a protected version of the aglycon ('allosamizoline') sector of allosamidin. An allal derivative stereoselectively reacted with benzenesulfonamide in the presence of a halonium source to afford a 2β-halo-1α-sulfonamidohexose. Treatment of this product with a strong base generated an intermediate 1,2-sulfonylaziridine, which was trapped with a protected allal derivative to provide a disaccharide glycal. Reiteration of this scheme gave access to the required trisaccharide. Following deprotection, the total synthesis of allosamidin was accomplished. In addition, the method, with modification, gave access to several allosamidin analogs.