1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose synthesis
- Product Name:1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose
- CAS Number:21740-23-8
- Molecular formula:C19H15Cl3O5
- Molecular Weight:429.67
80339-59-9
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21740-23-8
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Yield:21740-23-8 77%
Reaction Conditions:
with hydrogenchloride;acetic acid;acetyl chloride in 1,4-dioxane;chloroform at 13 - 15;Inert atmosphere;
Steps:
3
Example 3 Preparation of 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-alpha-D-ribofuranosyl-chloride.1-O-methyl-3,5-di-O-p-chlorobenzoyl-2-deoxy-alpha/beta-D-ribose (15.94 g), glacial acetic acid (60 mL), anhydrous chloroform (30 mL), anhydrous dioxane (30 mL) and acetyl chloride (0.87 g) were added into a 4-neck, 250 mL round-bottom flask. Under stirring and nitrogen, gaseous HCl was fed (11.5 g) subsurface while the temperature was maintained between 13 to 15° C. 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-alpha-D-ribofuranosyl-chloride slowly crystallized out during HCl feeding. The slurry was stirred at 12° C. for 20 minutes after HCl feeding was complete. The product was collected and rinsed with anhydrous hexanes (20 mL). After drying, 12.4 g of 1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-alpha-D-ribofuranosyl-chloride was isolated as white powder (77% yield).
References:
US2010/249394,2010,A1 Location in patent:Page/Page column 4-5