(4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE synthesis

9synthesis methods

Product Name:(4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE
CAS Number:14131-42-1
Molecular formula:C20H23NO12
Molecular Weight:469.4

108-24-7
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3767-28-0 Synthesis

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(4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE

14131-42-1
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Yield:14131-42-1 95%

Reaction Conditions:

with pyridine;dmap at 20; for 16 h;

Steps:

Synthesis of 2,3,4,6-tetraacetyl-1-p-(N-succinyl)-aminophenyl-α-D-glucopyranoside (4)

General procedure: A mixture of p-nitrophenyl-α-D-glucopyranoside (1, 1.00 g, 3.32 mmol) and 5 equivalent of acetic anhydride (1.57 mL) and DMAP (4-dimethylaminopyridine, catalytic amount) in 7 mL of pyridine was stirred at room temperature for 16 h. After removal of pyridine, the residue was chromatographed on silica gel (2 x 25 cm, eluent volume ratio is n-hexane : ethyl acetate = 1:1) affording 2,3,4,6-tetraacetyl-1-p-nitropheyl-α-D-glucopyranoside (2, 1.50 g, 3.15 mmol, 95 % yield) as white solids. A mixture of 2 (1.50 g, 3.15 mmol) and catalytic amount of Pd/C in methanol (10 mL) was stirred at rt for 16 h under hydrogen atmosphere. After removal of Pd/C and solvent, the residue was mixed with succinic anhydride (630 mg, 2 equiv) and DIPEA (2.2 mL, 2 equiv) in DMF (6 mL). The resulting solution was stirred at rt for 3 h. After removal of DMF, the residue was chromatographed on silica gel (2 x 25 cm, eluent volume ratio is DCM : methanol = 20:1). Compound 4 was further purified on Waters HPLC. XBridge^TM C18 (5 mm, 19 x 150 mm) column was used as stationary phase. For the mobile phase, buffer A (water with 0.1% v/v TFA) and buffer B (acetonitrile with 0.1% v/v TFA) were used as a gradient. The gradient conditions are as follows: 5 min, 5% B followed by linear gradient 5-70% B over 30 min. Purification afforded 1.01 g (1.89 mmol, 60% yield) of 2,3,4,6-tetraacetyl-1-p-(N-succinyl)-aminophenyl-α-D-glucopyranoside 4 as white solid.

References:

Park, Sangeun;Hyun, Soonsil;Yu, Jaehoon [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 8,p. 2441 - 2444] Location in patent:supporting information; experimental part

100-02-7 Synthesis