ChemicalBook CAS DataBase List Methyl 2,3,4-Tri-O-isobutyryl-1-O-trichloroacetimidoyl-a-D-glucopyranuronate

Methyl 2,3,4-Tri-O-isobutyryl-1-O-trichloroacetimidoyl-a-D-glucopyranuronate synthesis

5synthesis methods

Product Name:Methyl 2,3,4-Tri-O-isobutyryl-1-O-trichloroacetimidoyl-a-D-glucopyranuronate
CAS Number:150607-96-8
Molecular formula:C21H30Cl3NO10
Molecular Weight:562.82

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α-D-Glucopyranuronic acid, methyl ester, 2,3,4-tris(2-methylpropanoate)

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Methyl 2,3,4-Tri-O-isobutyryl-1-O-trichloroacetimidoyl-a-D-glucopyranuronate

150607-96-8
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Yield:150607-96-8 75%

Reaction Conditions:

with potassium carbonate in dichloromethane; for 40 h;

Steps:

8.3

Step 3: Methyl 2,3,4-tri-O-isobutyril-1-O-trichloroacetimidoyl- -D-glucopyranuronate (4) To a stirred solution of methyl 2,3,4-tri-O-isobutyryl-D-glucopyranuronate 3 (418 g, 1 mmol) in CH₂Cl₂ (5 mL) was added trichloroacetonitrile (0.4 mL, 3.7 mmol), followed by anhydrous potassium carbonate (83 mg, 0.6 mmol), and the mixture stirred for 40h. It was filtered through a short pad of silica and eluted with ether. Filtration and evaporation in vacuo then yielded the title product 4 as a semi crystalline gum which crystallized from dry isopropanol as white prisms, mp 108°C (422 mg, 75%). δH (300 MHz, CDCl3): 8.72 (s, NH), 6.66 (d, J=3.5 Hz), 5.70 (t, J=10 Hz), 5.30 70 (t, J=10 Hz), 5.20 (dd, J=10,3.5 Hz), 4.51 (d, J=10 Hz), 3.75 (s, OMe), 2.60-2.43 (m, 3*CHMe₂), 1.17-1.06 (m, 3*CHMe₂).

References:

EP1777222,2007,A1 Location in patent:Page/Page column 27-28

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