- A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol
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3-Acetamido-5-amino-3,5,6-trideoxy-d-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-d-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-β-d-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale.
- Simak, Ondrej,Stanek, Jan,Moravcova, Jitka
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experimental part
p. 966 - 971
(2009/09/05)
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- Direct stereocontrolled synthesis of 3-amino-3-deoxy-β- mannopyranosides: Importance of the nitrogen protecting group on stereoselectivity
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(Chemical Equation Presented) The highly stereocontrolled synthesis of the 3-amino-3-deoxy-β-mannopyranosides is achieved by means of thioglycoside donors protected with a 4,6-O-benzylidene or alkylidene acetal and a benzylidene imine group. Among the var
- Crich, David,Xu, Huadong
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p. 5183 - 5192
(2008/02/08)
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- Synthesis of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-formyl-α-d- erythro-hex-2-enopyranoside
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The synthesis of the title compound was achieved in seven steps and 61% overall yield from methyl α-d-glucopyranoside.
- Mangione, María I.,Suárez, Alejandra G.,Spanevello, Rolando A.
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p. 149 - 153
(2007/10/03)
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