182204-85-9

Upstream product

• 1053526-71-8 [(S)-2-Benzyloxy-1-((4R,5R)-5-dodecyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-ethyl]-carbamic acid benzyl ester 
• 154659-19-5 (2S,3R,4R)-1-(benzyloxy)-2-hexadecane-3,4-diol 

Downstream Products

• 588-46-5 N-(phenylmethyl)acetamide 
• 182204-86-0 (4S,5S)-4-benzyl-5-((1R)-1-hydroxy-3-methylbutyl)-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Selective inversion of the proximal or distal hydroxyl groups in syn,syn-3-[N-(alkoxycarbonyl)ammo] 1,2-diols via cyclic sulfates

The formation of cyclic sulfates (4) from syn, syn-3-[N-(benzyloxycarbonyl)amino] 1,2-diols provides a common intermediate to access other diastereomers via two inversion procedures. Thermolysis of the cyclic sulfates in acetonitrile normally leads to inversion of the distal hydroxyl group to form a 1,3-oxazin-2-one (6). Catalytic hydrogenation of the cyclic sulfates under basic conditions (NEt3) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).