299172-62-6

Usage

Chemical Properties

Colourless Oil

InChI:InChI=1/C42H59NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-26-33-39(44)38(43-40(45)47-41(2,3)4)34-46-42(35-27-20-17-21-28-35,36-29-22-18-23-30-36)37-31-24-19-25-32-37/h17-33,38-39,44H,5-16,34H2,1-4H3,(H,43,45)/b33-26+/t38-,39+/m0/s1

Upstream product

• 15890-72-9 laurylmagnesium bromide 
• 76-83-5 trityl chloride 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 

Downstream Products

• 299172-58-0 3-O-benzoyl-N-tert-butoxycarbonyl-1-O-tritylsphingosine 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 299172-56-8 3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-stearoyl-D-erythro-sphingosine 
• 299172-60-4 [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine 
• 299172-48-8 [glucose-(13)C6]-1-O-(β-D-glucopyranosyl)-D-erythro-sphingosine 
• 4201-60-9 3-O-benzoyl-D-erythro-sphingosine 
• 41106-92-7 (2S,3R,4E)-3-O-benzoyl-2-octadecanamido-4-octadecene-1,3-diol 
• 18459-13-7 (2S,3R,4E)-3-O-benzoyl-N-trifluoroacetyl-4-sphingenine 

Relevant academic research and scientific papers

Enantio- and diastereoselective syntheses of 3-hydroxypiperidines through iridium-catalyzed allylic substitution

Stereoselective syntheses of 3-hydroxypiperidines have been developed. Key intermediates are N-protected allylamines that are prepared by an enantioselective iridium-catalyzed allylic amination. A subsequent catch and release procedure that involves an epoxidation and base-mediated elimination yields δ-lactams that are suitably functionalized to prepare biologically active 3-hydroxypiperidines. In addition, applications of this method to the total syntheses of deoxymannojirimycin, D-erythro-sphingosine, and chiral building blocks of interest for medicinal chemistry are described. Stereoselective syntheses of 3-hydroxypiperidines are reported. The key reactions are an iridium-catalyzed allylic amination and a catch and release procedure that consists of a highly diastereoselective epoxidation and a base-mediated ring opening of the epoxide. This method was applied to the total syntheses of sphingosine, deoxymannojirimycin, and pharmaceutically relevant small molecules. Copyright

Practical syntheses of [13C]- and [14C]-labelled glucosphingolipids

Synthetic routes to [glucose-U-14C]-1-O-(β-D-glucopyranosyl)-N-stearoyl-D-erythro-sp hingosine 1b and to [glucose-13C6]-1-O-(β-D-glucopyranosyl)sphingosine ([glucose-13C6]glucopsychosine, 2b) are described. Whereas the protected ceramide precursor for lb was prepared using conventional methodology, two new strategies were developed in the course of the synthesis of 2b. Of these, one relies on keeping a protecting group in place at all times to avoid the handling difficulties associated with sphingosine 4, while the other generates a protected derivative (24) of sphingosine indirectly by means of a Mitsunobu inversion.