ChemicalBook CAS DataBase List BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE

BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE synthesis

7synthesis methods

Product Name:BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
CAS Number:38416-56-7
Molecular formula:C36H39NO6
Molecular Weight:581.7

α-D-Glucopyranose, 2-(acetylamino)-2-deoxy-3,4,6-tris-O-(phenylmethyl)-, 1-acetate

4171-73-7
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100-51-6 Synthesis

100-51-6
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4171-69-1 Synthesis

Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

4171-69-1
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BENZYL 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE

38416-56-7
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$80.00/500mg

Yield:4171-69-1 49.6 mg ，38416-56-7 52.1 mg

Reaction Conditions:

with boron trifluoride diethyl etherate;ytterbium(III) triflate in dichloromethane at 20; for 16 h;Overall yield = 86 %;

Steps:

Typical glycosidation procedure

General procedure: Yb(OTf)3 (98.2 mg, 0.2 mmol) was added to a solution of 1 (101.4 mg, 0.2 mmol), 2 (19.34 mg, 0.2mmol), and BF3·OEt2 (47 μL, 0.005 mmol) in CH2Cl2 (3 mL) at 0°C, and the resulting mixture was stirred for 16 h at room temperature. The reaction was then quenched by the addition of sat. aq. NaHCO3 solution (5 mL), and the reaction mixture was extracted with CH2Cl2. The organic layer was then washed with water and sat. aq. NaCl solution and dried over Na2SO4, the solvent. The crude product obtained after evaporation of the solvent under reduced pressure was purified via preparative silica gel TLC(EtOAc/hexane = 2/1) to give 3 (95% yield, α form; 35.7 mg, β form; 53.7 mg, α/β ratio = 40/60) as white crystals.

References:

Oda, Yoshiki;Midorikawa, Masanobu;Yamanoi, Takashi [Heterocycles,2015,vol. 90,# 1,p. 198 - 215]

14146-27-1 Synthesis