Synthesis of Methyl 2,3,5-Tri-O-benzoyl-α[alpha]-d-arabinofuranoside in the Organic Laboratory

Propargyl/methyl furanosides as potential glycosyl donors

“…The optimum temperature was found to be 65 1C with acetonitrile as the solvent. Here again, we observed the same diastereoselectivities; for example, D-ribf (7) and D-lyxf (10) donors afforded 3a, 6a with 1,2-trans diastereoselectivity whereas D-xylf (8) and D-araf (9) resulted in glycosides 4a and 5a as a mixture of diastereomers. 9 Similar results were noticed when methyl furanosides (7-10) were reacted with other glycosyl acceptors 2b and 2c to furnish glycosylated products 3b, 3c, 4b, 4c, 5b, 5c, 6b, 6c in good yields (Table 2).…”

p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates

“…The 3,4-dimethylphenyl p -nitrophenyl carbonate ( 9a ) and geranyl carbonate 10a gave the corresponding γ-lactams 9b and 10b in 62% and 46% yields, respectively. Similarly, the p -nitrophenyl carbonate of D-psicofuranose [28], n -pentenyl 2,3,4-tri- O -benzyl-α-D-mannopyranoside [32–34] and 2,3-di- O -benzyl-α-methyl-D-arabinofuranoside [35] (Table 2, 11a–13a) gave the γ-lactam-derived carbamates 11b–13b in 53%, 63% and 67% yield, respectively.…”

Synthesis of substituted N-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory

“…The commitment of faculty to incorporating synthesis into the curriculum is evident in a large number of multi-step syntheses in Mayo's classic laboratory textbook (5) and the multitude of synthesis experiments found in the literature. These experiments provide a variety of approaches to teaching synthesis in the sophomore organic chemistry curriculum with most of them focusing on the synthesis of a biologically (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) or commercially (18)(19)(20)(21)(22)(23)(24) relevant target while some are designed for pedagogical (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37) reasons. The complexity of the syntheses differ greatly and range from two (6, 7, 11-13, 16, 18, 20, 22, 27, 31, 36), three (8, 10, 14, 15, 17, 21, 23, 25, 28-30, 34, 37), four (9,26,33,38), five (19,32), six (24,39), and eight (40) step processes.…”