1402155-06-9

Upstream product

• 54469-08-8 phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside 
• 74912-02-0 1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose 
• 102919-04-0 benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 
• 7677-24-9 trimethylsilyl cyanide 
• 100-46-9 benzylamine 
• 530-26-7 D-Mannose 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 

Downstream Products

• 1402155-08-1 C₁₈H₂₂N₂O₄ 

Relevant academic research and scientific papers

Polyhydroxyamino-piperidine-type iminosugars and pipecolic acid analogues from a D -mannose-derived aldehyde

A general strategy for the synthesis of diversely substituted 3,4,5-trihydroxypiperidines (including two natural products), 5-amino-3,4-dihydroxypiperidines, 3,4,5-trihydroxypipecolic acids, and 2-(aminomethyl)-3,4,5-trihydroxypiperidines is reported. The procedure used a double reductive amination or a Strecker reaction, starting from differently protected aldehydes readily synthesized on a gram scale from D-mannose. The biological activities of the target compounds were evaluated, and some of them showed moderate inhibition of α-L-fucosidase and β-glucosidase. The synthesis of diversely substituted polyhydroxypiperidines, polyhydroxyaminopiperidines, and trihydroxypipecolic acid derivatives is reported, using Strecker reactions and double reductive aminations, starting from a D-mannose-derived aldehyde. Copyright

Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines

A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio-and diastereoselective Strecker reaction.