136185-70-1

Upstream product

• 136185-63-2 (2S^*,3R^*)-1-(Benzyloxy)-3-iodohexan-2-ol 
• 100-39-0 benzyl bromide 
• 6920-22-5 Hexane-1,2-diol 
• 107076-91-5 (2S^*,3S^*)-1-(Benzyloxy)-2,3-epoxyhexane 
• 89395-00-6 2,3-epoxyhexan-1-ol 
• 1436-34-6 1,2-Epoxyhexane 
• 100-51-6 benzyl alcohol 

Downstream Products

• 832690-22-9 toluene-4-sulfonic acid 1-benzyloxymethyl-pentyl ester 

Relevant academic research and scientific papers

Synthesis of a potent hNK-1 receptor antagonist via an SN2 reaction of an enantiomerically pure α-alkoxy sulfonate

(Chemical Equation Presented) The concise synthesis of a stereochemically rich hNK-1 receptor antagonist is described. The synthesis is highlighted by an SN2 reaction of an enantiomerically pure α-alkoxy sulfonate (orthogonally protected butane triol), which was prepared by utilizing salen-mediated hydrolytic kinetic resolution technology. A stereocontrolled acetalization was employed to connect two enantiomerically pure fragments with a high degree of diastereoselectivity.

Regioselective benzylation of diols and polyols by catalytic amounts of an organotin reagent

An efficient one-pot method for the selective benzylation of diols and polyols using 0.1 equiv. of organotin reagents and tetrabutylammonium bromide as catalyst has been developed. The diols and polyols containing a cis-vicinal diol were regioselectively

Erbium(III) triflate is a highly efficient catalyst for the synthesis of β-alkoxy alcohols, 1,2-diols and β-hydroxy sulfides by ring opening of epoxides

Chemo- and stereoselectivity in the ring-opening reaction of epoxides with erbium(III) triflate are described. Epoxides can be cleaved under neutral conditions with alcohols and thiols in the presence of catalytic amounts of Lewis acid, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields.

Regioselective Opening of Epoxy Alcohols: Mild Chemo- and Stereoselective Preparation of Iodohydrins and 1,2-Diols

Several 2,3-epoxy alcohols have been opened, at -60 deg C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity.The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols.The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use.Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile.The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodiode ion.