Synthesis of 2,6-dideoxy-α-L-lyxo- and 2,6-dideoxy-α-L-arabino-hexopyranosyl halides

Synthesis of .epsilon.-rhodomycinone glycosides

“…The e-rhodomycinone was recrystallized from chloroform-cyclohexane until constant melting point (213 °C). The mass spectrum was in agreement with the tabulated data found in the literature.11 Synthesis of the Blocked Glycosides (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21). A suspension of the required glycosyl halide (1 g, 3.7 mmol), e-rhodomycinone (1 g, 2,3 mmol), mercuric bromide (830 mg, 2.3 mmol), mercuric Notes cyanide (60 mg, 230 Mmol), and finely ground 3A molecular sieves (5 g) in tetrahydrofuran (55 mL) was stirred and heated under reflux.…”

“…The rationale for testing the former compounds was that in the daunorubicin series, antitumor activity is enhanced by lipophilicity.7 Tests were made at Bristol Laboratories and at the National Cancer Institute. The compounds prepared were tested for antibiotic activity on Bacillus substilis which showed activity for the 2-deoxy-di-Oacetyl-D-ribopyranosyl-e-rhodomycinone (9). However, no induction was observed for any of the glycosides subjected to the ILB test.12 Antitumor activity on P388 lymphatic leukemia in CDF mice was observed for 2-deoxy-di-Oacetyl-D-ribopyranosyl-e-rhodomycinone (9) which had a T/C of 125 at a dose of 64 mg/kg/day and 110 at a dose of 128 and 32 mg/kg/day.…”

“…The compounds prepared were tested for antibiotic activity on Bacillus substilis which showed activity for the 2-deoxy-di-Oacetyl-D-ribopyranosyl-e-rhodomycinone (9). However, no induction was observed for any of the glycosides subjected to the ILB test.12 Antitumor activity on P388 lymphatic leukemia in CDF mice was observed for 2-deoxy-di-Oacetyl-D-ribopyranosyl-e-rhodomycinone (9) which had a T/C of 125 at a dose of 64 mg/kg/day and 110 at a dose of 128 and 32 mg/kg/day. The unblocked glycoside 25 had a T/C of 115 at a dose of 13 mg/kg/day.…”

Synthetic Approaches to Small Cluster Oligosaccharide Mimetics

“…All literature procedures have serious problems [32][33][34], among which solvolysis of the unstable intermediate glycosyl bromides is the major one.…”

Synthesis and Antiproliferative Evaluation of 2-Deoxy-N-glycosylbenzotriazoles/imidazoles

“…Glycals have been used extensively as building blocks in the preparation of 2-deoxy sugars via their hydration or hydro-alkoxylation catalyzed by methanolic hydrogen halide [ 14 , 15 , 16 ]. Other methods include the use of methane sulfonic acid as catalyst [ 17 ], enzymes [ 16 , 18 ], alkoxymercuration of a glycal followed by reduction with sodium borohydride [ 19 , 20 ] and halohydration followed by dehydrogenation [ 21 , 22 , 23 ]. More closely related to this study is the method developed by Kashyap and co-workers via the reaction of various protected d -glucal with a mixture of tetra- n -butylammonium iodide with sodium periodate to afford 2-deoxyglycosides [ 24 ].…”