Synthesis of 1-Deoxymannojirimycin from D-Fructose using the Mitsunobu Reaction

被引：3
|
作者：
Sunde-Brown, Peter [1 ]
Jenkins, Ian D. [3 ]
Houston, Todd A. [1 ,2 ]
机构：
[1] Griffith Univ, Inst Glyc, Southport, Qld 4215, Australia
[2] Griffith Univ, Sch Environm & Sci, Southport, Qld 4215, Australia
[3] Griffith Univ, Griffith Inst Drug Discovery, Nathan, Qld 4111, Australia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 24期
关键词：
ENZYME-CATALYZED REACTIONS; MANNOSIDASE INHIBITOR; STEREOSELECTIVE-SYNTHESIS; PRACTICAL SYNTHESIS; DEOXYMANNOJIRIMYCIN; PYRROLIDINES; DERIVATIVES; ACID;
D O I：
10.1021/acs.joc.2c02174
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three different Mitsunobu reactions have been investigated for the synthesis of 1-deoxymannojirimycin (1-DMJ) from D-fructose. The highest yielding and most practical synthesis can be undertaken on a 10 g scale with minimal chromatography. In the key step, N,O-di-Boc-hydroxylamine reacts with methyl 1,3-isopropylidene-alpha-D-fructofuranose under Mitsunobu conditions to give 14. Acidic hydrolysis affords nitrone 15, which reduces quantitatively via catalytic hydrogenolysis to afford 1-DMJ (4) in 55% overall yield from D-fructose (cf. 37% for azide route and 29% for nosyl route).
引用
收藏
页码：16895 / 16901
页数：7
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