1,2,3-triacetyl-5-deoxy-β-D-Ribose

Introduction

Product name 1,2,3-Triacetyl-5-deoxy-D-ribose

CAS No 62211-93-2

Molecular formula C11H16O7

Molecular weight 260.24

1,2,3-triacetyl-5-deoxy-β-D-Ribose is an important intermediate in the synthesis of Capecitabine. The raw material of Capecitabine can be prepared in three steps through the route reported in the literature. According to reports in the literature, the synthesis of triacetylribose mainly involves the following two methods: one is to use 1-methyl-5-deoxyribose as an intermediate and obtain triacetylribose through a two-step reaction; the other is to use 5-deoxy-D -Ribose is an intermediate and triacetyl ribose is obtained through one-step acetylation. According to the synthesis method reported above, the triacetyl ribose prepared is a mixture of α and β isomers. The β isomer participates in the next reaction to prepare capecitabine. The α isomer is the produced impurity, and its α isomer The proportion of conformers is 3~30%, and the proportion of α isomer will not be higher. Under this isomer ratio, pure β-isomer can be obtained through column chromatography or recrystallization. Preparation Method for preparing the alpha isomer of triacetyl ribose. The specific method uses 5-deoxy-D-ribose as the starting material, acetylation under the action of acrylate acetate/ferric chloride to obtain a mixture of triacetylribose isomers, and the mixture is further purified into the triacetylribose α-isomer. Pure. The reaction raw material 5-deoxy-D-ribose is a known compound, and its sample can be obtained through the synthesis method of patent WO2008/105593, using methyl-5-deoxy-2,3-O-isopropylidene-β-D - The sample is prepared by heating and hydrolyzing nucleoside (V) with sulfuric acid as raw material.

Usage: Intermediate of Capecitabine

Melting point 63-64°C

Boiling point 315°C

Density 1.23

Vapor Pressure 0.005-0.01 Pa at 20-25℃

Flash point 136°C

Storage condition Sealed in dry, 2-8°C

Solubility Soluble in ethanol

Form Powder

Color Yellow to Brown