138337-18-5

Upstream product

• 60-12-8 2-phenylethanol 
• 138337-13-0 N-(2-phenylethyl)sulfamic acid 
• 24281-43-4 sulfurous acid diphenethyl ester 
• 138337-15-2 potassium N-nitroso-N-(2-phenylethyl)sulfamate 

Downstream Products

• 474801-43-9 (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenethyloxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 474801-75-7 C₃₅H₅₀N₄O₁₃ 
• 474801-60-0 (4S,5R,6R)-5-Acetylamino-4-azido-6-((1S,2R)-2,3-diacetoxy-1-phenethyloxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and anti-influenza virus activity of 7-O-alkylated derivatives related to zanamivir

A series of 7-alkyl ether derivatives related to zanamivir were synthesized using direct alkylation of the C-7 alcohol of sialic acid. Alkyl ether moiety of less than 12 carbons in length showed low nanomolar inhibitory activity against influenza A virus sialidase. Furthermore, their moiety improved influenza A virus plaque reduction activity compared to zanamivir. However, removal of the 8,9-diol of the 7-O-alkyl derivatives resulted in loss of antiviral potency. This result suggests that 8,9-diol must play an important role in binding with both influenza A and B virus sialidases.

N-Nitrososulfamates: Sources of Carbonium Ions in Aqueous Media and Substrates in Solid-State Decompositions

Potassium N-nitrososulfamates of benzylamine, 2-phenylethylamine, and cyclohexylamine 2a-c were synthesized and examined as sources of carbonium ions in aqueous media.The nitrososulfamates are crystalline compounds which decompose readily at low pHs (ca. 2) under conditions where the parent amines are relatively stable to nitrous acid.In water solutions they produce the corresponding alcohols, principally, along with small percentages of the corresponding esters of potassium bisulfate.The decomposition of the benzyl analogue 2b in the presence of sodium thiocyanate produced, principally, benzyl alcohol, but also benzyl thiocyanate and benzyl isothiocyanate in a ratio of 4.4/1, indicating a muted role for nucleophilicity in this carbonium ion reaction.In sulfate buffers they decompose by pseudo-first-order kinetics (rate constants are reported).In acetic acid they produce principally the corresponding acetate esters.A reaction mechanism is proposed in which the slow step involves the production of a diazohydroxide rather than a direct formation of a carbonium ion.The benzyl analogue 2b is an inhibitor of the enzyme pepsin; it also undergoes a photoelimination reaction on irradiation.The nitrososulfamates are perfectly stable when dry, but they undergo a relatively rapid solid-state decomposition (T1/2 ca. 2-5 days) when exposed to normal atmospheric humidity; surprisingly, the external appearence of the crystals does not change during the decompositions.The products are, principally, the esters of sulfuric acid and potassium bisulfate.