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

Synthesis of a sucrose dimer with enone tether; a study on its functionalization

• Zbigniew Pakulski,
• Norbert Gajda,
• Magdalena Jawiczuk,
• Jadwiga Frelek,
• Piotr Cmoch and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

• shown in Figure 2. The properly activated sugar is converted into phosphorane or phosphonate which – upon reaction with an aldehyde derived from another monosaccharide – provides higher carbon sugar (HCS) enone [16][17][18]. Application of this methodology to selectively protected 2,3,3’,4,4’-penta-O

• ). Functionalization of the three-carbon atom unit connecting the C5-positions of both sucrose units required reduction of the carbonyl group of the enone system and oxidation of the double bond. We have already reported that reduction of higher carbon sugar enones of the D series with zinc borohydride is highly