Human T-Cell Leukemia Virus Type 1 (HTLV-1)

The practical synthesis of β-acyl glucuronides by using allyl 2,3,4-tri-( O -allyloxycarbonyl)- d -glucuronate and 1-chloro- N , N ,2-trimethyl-1-propenylamine

“…It has been reported that 1-chloro-N,N,2-trimethyl-1-propenylamine (TMCE) would form reactive carboxymethyleneiminium chloride with carboxylic acid, and that it reacts with organometallic compounds to give ketones in good yield. 12 As expected, treatment of KRP-105 (1) with TMCE at room temperature for 4 h followed by stirring with 5 in the presence of Et 3 N gave the desired acyl conjugate 8 with high β-selectivity (β/α = 97/3) (entry 3). The yield of 8 was improved when 2 eq.…”

“…15 On the other hand, in a more polar solvent, such as a mixture of THF and CH 2 Cl 2 (3:1), TMCE reacts with carboxylic acids to form the carboxymethyleneiminium chloride without liberation of hydrogen chloride. 12 As shown in Scheme 5, treatment of 5 with benzoyl chloride (25) in THF afforded corresponding acyl conjugate 13b/13c with lower β-selectivity (β/α = 4/1). In contrast, adding 5 into pre-mixed TMCE and benzoic acid (13a) in THF gave 13b/13c with high β-selectivity ( Table 2, entry 1; β/α = 94/6).…”