213531-28-3

Upstream product

• 221697-40-1 Methanesulfonic acid (S)-1-(4-methoxy-phenoxymethyl)-2-trityloxy-ethyl ester 
• 220641-16-7 1-O-(triphenylmethyl)-3-O-(4'-methoxyphenyl)-sn-glycerol 
• 927827-64-3 1-((R)-2-Azido-3-trityloxy-propoxy)-4-methoxy-benzene 
• 17131-52-1 (R)-3-(p-methoxyphenoxy)-1,2-propanediol 

Relevant academic research and scientific papers

Regioselective and Stereospecific Azidation of 1,2- and 1,3-Diols by Azidotrimethylsilane via a Mitsunobu Reaction

A one-pot regio- and stereospecific azidation reaction of 1,2- and 1,3-diols with azidotrimethylsilane (MB3SiN3) via a Mitsunobu reaction has been achieved. With 1,2- and 1,3-diols, the reaction of triphenylphosphine, diisopropyl azodicarboxylate, and Me3SiN3 in dichloromethane gave regioselective azidation at C-2 and C-3, respectively, in good yield (74-90% combined yield of 1a + 1b or of 2a + 2b). However, application of the same reaction conditions to a 1,4-diol led to the exclusive formation of the cyclic ether. The regioselectivity of this one-pot reaction is influenced by the solvent, the degree of steric bulk at C-2 of the 1,2-diol or at C-3 of the 1,3-diol, and the presence of electron-donating and electron-withdrawing groups near the secondary carbinol carbon. This selectivity is discussed in terms of the mechanistic model proposed by Mathieu-Pelta and Evans (Mathieu-Pelta, I.; Evans, S. A., Jr. J. Org. Chem. 1992, 57, 3409-3413), which involves reaction of the dioxaphospholane intermediate with Me3SiN3 to form oxyphosphonium ions 4 and 5.

Synthesis and Absolute Configuration of a Novel Aminoglycoglycerolipid, Species-Specific Major Immunodeterminant of Mycoplasma fermentans

In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their 1H-1H-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. - Keywords: amino-alcohols; glycolipids; immunodeficiency; phospholipids; phosphoramidites