58886-34-3

Upstream product

• 70678-13-6 1,2-bis(1-isocyanato-1-methylethyl)diazene 
• 100-51-6 benzyl alcohol 
• 908094-04-2 phenyldiazomethane 
• 67-64-1 acetone 
• 65-85-0 benzoic acid 
• 38636-02-1 N-benzyl-O-benzoylhydroxylamine 
• 126-84-1 2,2-diethoxypropane 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 90406-05-6 2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-arabino-hexose dibenzyl acetal 
• 73707-69-4 2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dibenzyl acetal 
• 73707-69-4 [(R)-2,2-Bis-benzyloxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-carbamic acid benzyl ester 
• 90406-08-9 2-deoxy-2-(2,4-dinitrophenyl)amino-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dibenzyl acetal 
• 185383-34-0 (5R,6S,7S)-5,7-dibenzyloxy-6-[(t-butyldimethylsilyl)oxy]cyclohepta-1,3-diene 
• 1227489-30-6 (Z)-N-[3-(1-benzyloxy)-2,3dimethylbutylidede]-2-methylpropan-2-amine oxide 
• 119694-98-3 4-(benzyloxy)-β-carboline 
• 32783-20-3 benzyl isopropenyl ether 
• 90406-06-7 2-deoxy-3,4:5,6-di-O-isopropylidene-2-(trifluoroacetamido)-aldehydo-D-glucose dibenzyl acetal 
• 90406-07-8 2-deoxy-2-(hexadecanoylamino)-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dibenzyl acetal 
• 73707-68-3 N-[(R)-2,2-Bis-benzyloxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-acetamide 
• 73707-68-3 2-acetamido-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dibenzyl acetal 
• 58886-40-1 benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 

Relevant academic research and scientific papers

Lymph-Node-Targeted Immune Activation by Engineered Block Copolymer Amphiphiles-TLR7/8 Agonist Conjugates

Small molecule immuno-modulators such as agonists of Toll-like receptors (TLRs) are attractive compounds to stimulate innate immune cells toward potent antiviral and antitumor responses. However, small molecules rapidly enter the systemic circulation and

N-Trimethylsilyloxyenamines as new aldehyde enolate synthons: General, efficient and diastereoselective aldol reaction with ketals and acetals

(E)-N-Trimethylsilyloxyenamines, easily accessible from aldonitrones, proved to be excellent nucleophiles in TMSOTf-induced diastereoselective aldol reaction, both with ketals and acetals, proceeding via an extended transition state and leading to a new aldol C-C-bond in the aldonitrone products, that can be readily hydrolysed to the corresponding aldehydes.

Interception of deaminatively generated benzyl carbenium ions by acetone

Essentially free benzyl carbenium ions were generated via protonation of phenyldiazomethane with benzoic acid in acetone. Interestingly, no proton transfer occurred below -20 °C. After protonation and dediazoniation of the diazoalkane at -20 °C, the solvent was found to intercept the deaminatively generated carbocations to yield initially the corresponding O-benzyl oxonium ion and benzyl benzoate. The onium ion, however, was labile under the reaction conditions, and decomposed into a cascade of products whose concentrations as a function of time were used to trace the reaction pathway. Thus, the O-benzyl oxonium ion reacted with benzoate ion to yield (2- benzyloxy)isopropyl benzoate; subsequent decomposition of this O-benzyl-O- benzoyl ketal produced 2,2-dibenzyloxypropane (a dibenzyl ketal), 2- benzyloxypropene, and benzyl alcohol. In a related study, benzyl cations were generated via thermolyses of N-benzyl-N-nitroso-O-benzoyl hydroxylamine at 0 and -70 °C. The product distributions were found to be temperature-dependent and different from that in the PhCHN2 + PhCO2H case.

ALCOHOLYSIS OF 1,2-BIS(1-ISOCYANATO-1-METHYLETHYL)DIAZENE: UNEXPECTED FORMATION OF 5,5-DIMETHYL-1,2,4-TRIAZOLIN-2-ONE

From the reaction of the bis(isocyanatoalkyl)diazene 1 with alcohols the expected adducts 2 could not be isolated (though there is spectroscopic evidence of their formation).The main product obtained was the triazolin-3-one 3, and in addition, several complementing products 4-6 were formed.