Synthesis of myrtenyl 6OaLarabinopyranosyl PDglucopyranoside 89 Sacranoside A

7eri-butyldimethylsilylation of 53 gave a silyl ether (91, 57% yield), which was subjected to benzoylation to give a benzoate (92) in 98% yield. Desilylation of 92 using 1 M HCl provided the desired 93 in 79% yield. By applying the

Sacranoside I

Figure 17: Structure of sacranosides A and B.

Sacranoside I

Figure 17: Structure of sacranosides A and B.

Figure 19: Synthesis of sacranoside B.

reported procedure, coupling reaction of myrtenyl P-D-glucopyranoside congener (93) and 2,3,4-tri-O-benzoyl-P-L-arabinopyranosyl bromide in the presence of AgOTf and TMU gave the corresponding coupling product (94) in 74% yield. Finally, treatment of 94 with NaOMe in MeOH provided the synthetic myrtenyl 6-O-a-L-arabinopyranosyl-P-D-glucopyranoside (89) in 44% yield.

3.7.2. Synthesis of neryl 6-O-a-L-arabinopyranosyl-fi-D-glucopyranosi.de (90) (Sacranoside B)

7eri-butyldimethylsilylation of 52 gave a silyl ether (95, 80% yield), which was subjected to benzoylation to give a benzoate (96) in 98% yield. Desilylation of 96 using 1 M HCl provided the desired 97 in 93% yield. The coupling reaction of neryl P-D-glucopyranoside congener (97) and 2,3,4-tri-O-benzoyl-P-L-arabinopyranosyl bromide in the presence of AgOTf and TMU gave the coupled product (98) in 96% yield. Finally, treatment of 98 with NaOMe in MeOH provided the synthetic neryl 6-O-a-L-arabinopyranosyl-P-D-glucopyranoside (90) in 48% yield.

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