5-O-CARBOMETHOXY-1,2-O-ISOPROPYLIDENE-D-XYLOFURANOSE synthesis

10synthesis methods

Product Name:5-O-CARBOMETHOXY-1,2-O-ISOPROPYLIDENE-D-XYLOFURANOSE
CAS Number:5432-33-7
Molecular formula:C10H16O7
Molecular Weight:248.23

α-D-Xylofuranose, 1,2-O-(1-methylethylidene)-, 3-(methyl carbonate)

1388092-19-0
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5-O-CARBOMETHOXY-1,2-O-ISOPROPYLIDENE-D-XYLOFURANOSE

5432-33-7
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$68.00/1g

Yield:5432-33-7 95%

Reaction Conditions:

with aluminum oxide in ethanol;chloroform;Column chromatography;

Steps:

4.7.1. 1,2-O-Isopropylidene-3-O-methylcarbonate-α-d-xylofuranoside (3d)

For the reaction was used 80.0 mg (0.22 mmol) of 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-3-O-methylcarbonate-α-d-xylofuranoside 1b, 2.00 mg (0.011 mmol) of CuCl₂·2H₂O and 2.2 mL of acetone/H₂O (95/5). The reaction led to a formation of 3d (55.0 mg, 100%). Purification by neutral alumina column chromatography of 40 mg (gradient from 98/2 to 95/5, v/v, CHCl₃/EtOH) led to an isolation of 38.0 mg of 1,2-O-isopropylidene-5-O-methylcarbonate-α-d-xylofuranoside 3a.

References:

Dvorakova, Marcela;Pribylova, Marie;Pohl, Radek;Migaud, Marie E.;Vanek, Tomas [Tetrahedron,2012,vol. 68,# 33,p. 6701 - 6711] Location in patent:experimental part