Dichloromethyl Methyl Ether

Henegar, Kevin E.; Quintero, Leticia; Meza-León, Rosa L.

doi:10.1002/047084289x.rd129.pub2

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“…Direct conversions of thioglycosides into glycosyl chlorides by using chlorine gas, 10 1,1-dichloromethyl methyl ether (MeOCHCl 2 )/ZnCl 2 , 11 iodine monochloride (ICl), 12 or oxalyl chloride/diphenyl sulfoxide 13 have been previously reported (Scheme 1 A). Despite their high efficiencies, the adoption of these procedures is limited as they require chlorine gas or volatile and corrosive reagents.…”

Section: Table 1 Optimization Of the One-pot Synthesis ...mentioning

confidence: 99%

One-Pot Synthesis of Glycosyl Chlorides from Thioglycosides Mediated by a Bromodiethylsulfonium Salt as a Mild Oxidant

Chooppawa

Janprasert

Padungros

2022

Synlett

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Conventional synthesis of glycosyl chlorides from thioglycosides relies on the two sequential oxidation and chlorination. A one-pot synthesis of glycosyl chlorides is warranted as an alternative method. Herein, we report the one-pot synthesis of glycosyl chlorides from thioglycoside precursors. The transformation was mediated at low temperature by bromodiethylsulfonium bromopentachloroantimonate (BDSB) as a mild oxidant and n-Bu4NCl as an additive. The armed thioglycosides afforded the corresponding α-glycosyl chlorides in moderate to good yields under the optimized conditions. Low conversions and yields were obtained when the less reactive disarmed thioglycosides were used. Unexpectedly, BDSB-mediated oxidation of thioglycosides without the addition of n-Bu4NCl also afforded the α-glycosyl chlorides in moderate yields. We suggest a mechanism involving the transfer of chloride ions from the non-nucleophilic bromopentachloroantimonate (SbCl5Br) anion to the oxocarbenium ion.

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Section: Table 1 Optimization Of the One-pot Synthesis ...mentioning

confidence: 99%