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Chemical Structure| 162491-62-5 Chemical Structure| 162491-62-5

Structure of 162491-62-5

Chemical Structure| 162491-62-5

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Product Details of [ 162491-62-5 ]

CAS No. :162491-62-5
Formula : C6H12O5
M.W : 164.16
SMILES Code : O[C@H]1[C@H](CO)OC(OC)[C@H]1O

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Application In Synthesis of [ 162491-62-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 162491-62-5 ]

[ 162491-62-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 67-56-1 ]
  • [ 24259-59-4 ]
  • [ 162491-62-5 ]
YieldReaction ConditionsOperation in experiment
This compound is prepared from <strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> according to Recondo and Rinderknecht (loc. cit.) who prepared 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (1, R1=Ac, R2=Bz) from <strong>[24259-59-4]D-<strong>[24259-59-4]ribose</strong></strong>. A mixture of <strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (150 g, 1.0 mol) in methanol (2.5 L) containing 1percent hydrogen chloride is stirred for 2 hours, and then neutralized with pyridine (250 mL). The mixture is concentrated in vacuo, and the residue dissolved in pyridine (1 L). To the solution is added benzoyl chloride (385 mL, 3.3 mol) dropwise while chilling to 0° C. After being kept overnight at room temperature, the mixture is concentrated in vacuo at 35-40° C. , and the residue is dissolved in ethyl acetate (1.5 L). The organic solution is washed successively with cold water (2.x.0.5 L), 1N H2SO4 (3.x.0.5 mL), water (0.5 L), saturated sodium bicarbonate (2.x.0.5 mL), dried over magnesium sulfate, concentrated in vacuo to a syrup which is dissolved in a mixture of glacial acetic acid (200 mL) and acetic anhydride (0.5 L). To the solution is added concentrated sulfuric acid dropwise at 0° C. The product solidified is filtered, washed successively with cold water (2.x.0.5 L), saturated sodium bicarbonate (2.x.0.5 L), cold water (2.x.0.5 L), and recrystallized from methanol to give compound 1 (225 g, 45percent), mp 124-125° C. . The 1H-NMR spectrum of this sample is identical to that of the D-isomer.
 

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