A new protecting group and linker for uridine ureido nitrogen

Abstract

(2,6-Dichloro-4-methoxyphenyl) (2,4,6-trichlorophenyl) methoxymethyl chloride [1, monomethoxydiphenylmethoxylmethyl chloroide (MDPM-Cl)] shows a significant relative stability and 1 reacts with uridine ureido nitrogen in the presence of DBU to form the corresponding protected uridine 8 in 95% yield. The MDPM-protected uridines are stable to a wide variety of conditions utilized for the synthesis of analogs of capuramycin and muraymycins. Significantly, the MDPM protecting group can conveniently be deprotected by using 30% TFA in CH2Cl2. In addition, polymer-bound MDPM-Cl 23 is useful for immobilization of uridine derivatives.

One‐Pot Protection‐Glycosylation Reactions for Synthesis of Lipid II Analogues

“…[10] Loading of the diol 6a onto the linker resin 4 was completed with BF 3 •OEt 2 (5 equivalents) at room temperature in 1h; in this step, progress of the reaction was monitored by consumption of 6a via LC-MS. Once the loading step was completed, the imidate 5a was added into the reaction mixture to afford the desired β-glycoside resin 7e in 65–80% yield which was determined based on the isolated 7a (Table 1) after the cleavage of 7e with 30% TFA in CH 2 Cl 2 for 1h. Accordingly, convenient synthetic procedures for 7d and 7e for the syntheses of lipid II analogues were accomplished.…”

Novel FR-900493 Analogues That Inhibit the Outgrowth of Clostridium difficile Spores

“…The monomethoxytetrachlorodiphenylmethoxymethyl (MTPM)-protected uridine 13 was prepared according to the previously reported procedure. 36 The primary alcohol of 13 was oxidized by a modified Swern condition to provide the corresponding aldehyde in a quantitative yield, which was then subjected to Carreira’s asymmetric alkynylation reaction using (−)- N -methylephedrine, 37 furnishing the ( S )-propargyl alcohol 14 in 80% yield with a selectivity of >98:2. The stereochemistry of the secondary alcohol of 14 generated via Carreira’s alkynylation was determined by the advanced Mosher’s method (see the Supporting Information ).…”

Efficient and Convenient Palladium‐Catalyzed Amination of Allylic Alcohols with N‐Heterocycles

“…It is well‐known that several uridine‐containing N‐heterocyclic natural products possess antitumor, antiviral, and antifungal properties 16. 17 Selected examples of such compounds are the thymidine analogue AZT, which is used for the treatment of AIDS;16a Eniluracil,16b which is widely used as anticancer drug; Capuramycin;16c FR‐900493;16d and Caprazol 16d. Moreover, uridine and its analogues are used for the synthesis of complex nucleoside antibiotics for drug development 17a–d.…”