Skip to main content
. 2024 Apr 5;89(8):5573–5588. doi: 10.1021/acs.joc.4c00067

Table 2. Redevelopment of the IMA for the Less Reactive Aldose l-Glycero-d-manno-heptose (11).

graphic file with name jo4c00067_0014.jpg

graphic file with name jo4c00067_0020.jpg

a

Reaction monitoring via TLC (CHCl3/MeOH/H2O 14:7:1)—product was not isolated.

b

Barbier-type protocol: 11 (1 equiv) in dry EtOH (0.1 M), 48 °C, subsequent addition of In (3 equiv) and 9 (4.5 equiv).

c

Barbier-type protocol: 11 (1 equiv) in dioxane/H2O (8:1, 0.1 M), 60 °C, subsequent addition of In (2 equiv) and 20 (entry 2) or 21 (entry 3) (3 equiv).

d

Grignard-type protocol: step 1—In (2 equiv) in dry THF (0.8 M), addition of 20 (entry 4) or 21 (entry 5) at 0 °C, then rt, 45 min; step 2—addition of 11 (1 equiv) in acid phthalate buffer (pH 3) (2.7 M), rt, 45 min.