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. 2017 Apr 28:13:795-799.
doi: 10.3762/bjoc.13.79. eCollection 2017.

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

Yan Chen  1 , Xiaoman Wang  1 , Junchang Wang  1 , You Yang  1
Affiliations

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

Yan Chen et al. Beilstein J Org Chem. .

Abstract

A [4 + 3] synthesis of D-manno-heptulose is described. The cascade 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: D-manno-heptulose; aldol reaction; cascade reaction; higher-carbon sugar; ketoheptose.

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Figures

Scheme 1
Scheme 1
Retrosynthetic analysis of D-manno-heptulose.
Scheme 2
Scheme 2
Initial attempt on the synthesis of the C4 aldehyde from D-lyxose (5).
Scheme 3
Scheme 3
Synthesis of differentially protected ketoheptose building block 2.
Scheme 4
Scheme 4
Synthesis of D-manno-heptulose (1).
See this image and copyright information in PMC

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