4704-76-1

Upstream product

• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 14593-43-2 benzyl allyl ether 

Downstream Products

• 137618-52-1 4-(benzyloxy)-3-hydroxybutanenitrile 
• 50610-95-2 1-benzyloxy-2-hydroxy-3-phenoxypropane 
• 99789-33-0 1-Benzyloxy-3-phenylthio-2-propanol 
• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 6972-79-8 dibenzyl glycerol 
• 150855-02-0 1-Benzyloxy-3-(naphthalen-1-yloxy)-propan-2-ol 
• 63473-97-2 2-hydroxy-3-benzyloxy-N-benzyl-1-propanamine 
• 99805-19-3 (R,S)-1-azido-3-benzyloxy-2-propanol 
• 176094-54-5 (S)-4-(Benzyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane 
• 93950-95-9 1-benzyloxy-2-carbamoyloxy-3-(2-methoxy-phenoxy)-propane 
• 176094-67-0 4-benzyloxy-1,1-dibromo-3-hydroxy-butane 
• 93728-27-9 1-benzyloxy-3-(2-methoxy-phenoxy)-propan-2-ol 
• 19343-24-9 F₀₀₅₀-0006 

Relevant academic research and scientific papers

Chemo- and Regioselective Functionalization of Polyols through Catalytic C(sp3)-C(sp3) Kumada-Type Coupling of Cyclic Sulfate Esters

This contribution describes a copper-catalyzed, C(sp3)-C(sp3) cross-coupling reaction of cyclic sulfate esters, a distinct class of electrophilic derivatives of polyols, with alkyl Grignard reagents to afford functionalized alcohol products in good yields. The method is operationally simple and highlights the potential of cyclic sulfate esters as highly reactive substrates in catalytic, chemoselective polyol transformations.

Synthesis of 1,1-dibromo-3-hydroxyalkanes via opening of cyclic sulfates

3-Alkoxy-1,1-dibromoalkanes are interesting substrates for diastereoselective bromine/lithium exchange reactions. A general route to the precursor 1,1-dibromo-3-hydroxyalkanes is described here via reaction of dibromomethyllithium with cyclic sulfates of 1,2-diols.

Nucleophilic Addition to Cyclic 1,2-Sulfites

Addition of heteroatom nucleophiles has been shown to attack at either the C5- or the S-atom sites in 4-(benzyloxymethyl)-1,3-dioxa-2-thiolane 2-oxide.No C4-reactivity was observed.The regioselectivity depended on the type of nucleophile.