1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE synthesis

4synthesis methods

Product Name:1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE
CAS Number:6619-10-9
Molecular formula:C21H26O12S
Molecular Weight:502.49

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98-59-9 Synthesis

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1,2,3,4-TETRA-O-ACETYL-6-O-TOSYL-BETA-D-GLUCOPYRANOSE

6619-10-9
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Yield:6619-10-9 39%

Reaction Conditions:

Stage #1: D-Glucose;p-toluenesulfonyl chloridewith pyridine at 0; for 20 h;Inert atmosphere;
Stage #2: acetic anhydride at 0 - 20; for 1 h;Inert atmosphere;

Steps:

1,2,3,4-Tetra-O-acetyl-6-O-p-toluenesulfonyl-β-D-glucopyranose (6-Ts-O-Ac-Glc)

D-Glucose12(500 mg, 2.8 mmol) was added to a solution ofp-toluenesulfonyl chloride (TsCl, 534 mg, 2.8 mmol) in anhydrous pyridine (7.5 mL) at 0°Cunder nitrogen atmosphere and the solution was stirred overnight. Then, Ac₂O (2.2 mL) was added dropwise and the solution was allowed to warm to room temperature. After 1h the solvent was removed in reduced pressure and the residue was dissolved in CH₂Cl₂. The solution was washed several times with saturated NaHCO₃aq., 0.2 M HCl aq. and water, dried under Na₂SO₄, and concentrated. The resulted crude 1,2,3,4-tetra-O-acetyl-6-O-p-toluenesulfonyl-β-D-glucopyranose (6-Ts-O-Ac-Glc) was crystallized from EtOH (0.54 g, 39%) as white solid.

References:

Fadlan, Arif;Tanimoto, Hiroki;Ito, Tatsuya;Aritomi, Yusuke;Ueno, Maho;Tokuda, Masaya;Hirohara, Shiho;Obata, Makoto;Morimoto, Tsumoru;Kakiuchi, Kiyomi [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 8,p. 1848 - 1858] Location in patent:supporting information

37074-90-1 Synthesis