1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose Chemical Properties

Melting point:

110-118°C (dec.)

Boiling point:

530.6±50.0 °C(Predicted)

Density 

1.46±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

color 

White to Off-White

Stability:

Not stable in Solution

InChI

InChI=1/C19H15Cl3O5/c20-13-5-1-11(2-6-13)18(23)25-10-16-15(9-17(22)26-16)27-19(24)12-3-7-14(21)8-4-12/h1-8,15-17H,9-10H2/t15-,16+,17-/s3

InChIKey

QEHCZULNFYDPPL-KIQRZSAINA-N

SMILES

C([C@H]1O[C@H](Cl)C[C@@H]1OC(C1C=CC(Cl)=CC=1)=O)OC(C1C=CC(Cl)=CC=1)=O |&1:1,3,6,r|

1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose Usage And Synthesis

Chemical Properties

1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose is White Solid

Uses

Intermediate used in the synthesis of nucleotide analogs.Unstable in solution!

Uses

1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose is used in the synthesis of nucleotide analogs. Unstable in solution!

Synthesis

Example 3: Preparation of 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-α-D-ribofuranosyl chloride To a 250 mL four-necked round-bottomed flask under nitrogen protection was added 1-O-methyl-3,5-di-O-(p-chlorobenzoyl)-2-deoxy-α/β-D-ribofuranose (15.94 g), glacial acetic acid (60 mL), anhydrous chloroform (30 mL), anhydrous dioxane (30 mL) and acetyl chloride (0.87 g). Under stirring conditions, gaseous HCl (11.5 g) was slowly passed while the reaction temperature was controlled between 13 and 15 °C. During this process, 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-α-D-ribofuranosyl chloride was gradually crystallized and precipitated.After the completion of HCl passage, the reaction mixture was continued to be stirred at 12 °C for 20 min. Subsequently, the product was collected by filtration and washed with anhydrous hexane (20 mL). After drying, 12.4 g of the target compound 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-α-D-ribofuranosyl chloride was obtained as a white powder in 77% yield.

References

[1] Patent: US2010/249394, 2010, A1. Location in patent: Page/Page column 4-5

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