693288-26-5

Upstream product

• 100-39-0 benzyl bromide 
• 693288-25-4 (2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)heptadecan-3-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 693288-28-7 methyl (2S)-N-methyl-2-(tert-butoxycarbonylamino)-3-(t-butyldimethylsilanyloxy)propanohydroxamate 
• 693288-24-3 (2S)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)heptadecan-3-one 
• 693288-29-8 (2S)-2-(t-butoxycarbonylamino)-1-hydroxyheptadecan-3-one 
• 122709-20-0 N-(tert-butoxycarbonyl)-L-serine N'-methoxy-N'-methylamide 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 

Relevant academic research and scientific papers

Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide

Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.