Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside synthesis

4synthesis methods

Product Name:Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside
CAS Number:85618-26-4
Molecular formula:C22H36O9S
Molecular Weight:476.58

111-88-6
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$15.00/25g

604-69-3 Synthesis

604-69-3
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$10.00/25g

Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside

85618-26-4
22 suppliers
$75.00/250mg

Yield:-

Reaction Conditions:

with indium(III) bromide in chloroform;Reflux;

Steps:

10

General procedure: Peracetyl-β-D-glycopyranose (1-5, 10mmol), InBr₃ (106mg, 0.3mmol, 0.03eq), and alkane-1-thiol (20mmol, 2eq) were suspended in CHCl₃ (7mL). The reaction mixture was heated to reflux with magnetic stirring. The course of the reaction was followed by TLC (hexane:EtOAc 1:1). After 1 hour the peracetate starting material could no longer be detected by TLC. The reaction was cooled to RT, diluted with CH₂Cl₂ (20mL), and this solution was applied to a short column (4cm×12cm) of SiO₂. The HOAc that was formed from the reaction and the excess alkane-1-thiol were eluted with hexanes. The desired thio-glycoside peracetate was eluted with hexanes:EtOAc 7:3. The fractions containing the desired material were combined, concentrated in vacuo, and the intermediate peracetates (12-14, 16-28) were characterized by 1D, 2D, ¹H-NMR and ¹³CNMR in CDCl₃ (in Tables in Supplementary data)

References:

Szabó, Lajos Z.;Hanrahan, Dillon J.;Jones, Evan M.;Martin, Erin;Pemberton, Jeanne E.;Polt, Robin [Carbohydrate Research,2016,vol. 422,p. 1 - 4]