174272-16-3

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 174272-15-2 (2R,3S,4R)-3-hydroxy-4-hydroxymethyl-2-(p-tolylsulfonamido)-4-butanolide 
• 174272-12-9 2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester 
• 174272-14-1 1,6-anhydro-3-deoxy-3,4-N,O-isopropylidene-3-(p-tolylsulfonamido)-β-D-ribo-hexopyranos-2-ulose 
• 174272-13-0 1,6-anhydro-3-deoxy-3,4-N,O-isopropylidene-3-(p-tolylsulfonamido)-β-D-altropyranose 
• 163356-94-3 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose 

Downstream Products

• 174272-17-4 (3aR,6R,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-3-(toluene-4-sulfonyl)-tetrahydro-furo[3,4-d]oxazol-4-one 
• 174272-18-5 (R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-[(4S,5S)-4-hydroxymethyl-2,2-dimethyl-3-(toluene-4-sulfonyl)-oxazolidin-5-yl]-ethanol 
• 174272-23-2 (2S,3S,4R)-2-(p-tolylsulfonamido)-1,3,4-octadecanetriol 
• 554-62-1 D-ribo-phytosphingosine 

Relevant academic research and scientific papers

Novel synthesis of phytosphingosine from levoglucosenone

Phytosphingosine, (2S,3S,4R)-2-amino-1,3,4-octadecanetriol was prepared in 8.6percent overall yield in 17 steps from levoglucosenone (1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose) by reduction of the carbonyl group, selective cis-oxyamination on the carbon-carbon double bond, oxidation of the 2-mydroxyl group to the carbonyl group, regioselective Baeyer-Villiger oxidation, reduction of the afforded lactone to the linear amino alcohol, oxidation of the primary hydroxyl group to the aldehyde, introduction of the hydrocarbon chain using a Wittig reaction, hydrogenation of the resulting carbon-carbon-double bond, and deprotection. - Keywords: Phytosphingosine: 2-Amino-1,3,4-octadecanetriol: Levoglucosenone: cis-Oxyamination