Synthesis of D-manno-heptulose via a cascade aldol/hemiketalization reaction

• Yan Chen,
• Xiaoman Wang,
• Junchang Wang and
• You Yang

Beilstein J. Org. Chem. 2017, 13, 795–799, doi:10.3762/bjoc.13.79

• aldol/hemiketalization reaction of a C4 aldehyde with a C3 ketone provides the differentially protected ketoheptose building block, which can be further reacted to furnish target D-manno-heptulose. Keywords: aldol reaction; cascade reaction; D-manno-heptulose; higher-carbon sugar; ketoheptose

• protected ketoheptose building block is still attractive due to the versatile functionalization possibilities of the building block into various derivatives of D-manno-heptulose. A de novo synthesis has proved to be an attractive strategy to produce orthogonally protected carbohydrate building blocks from

• simple precursors [28][29][30][31][32][33][34][35][36][37][38][39]. Here, we report a [4 + 3] approach to access differentially protected ketoheptose building blocks, which enables the synthesis of D-manno-heptulose. As depicted in Scheme 1, D-manno-heptulose (1) could be obtained by global deprotection