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2-Deoxy-L-ribose C화학적 특성, 용도, 생산
화학적 성질
white to light beige crystalline powder
용도
2-Deoxy-L-ribose is an isomer of 2-Deoxy-D-ribose (D252000) which induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione.
생산 방법
The provides the synthetic process of 2-Deoxy-L-ribose comprising the steps of; (A) protection step in which aldehyde group of 2-deoxy-D-ribose is protected in the form of acetal. 2-deoxy-l-O-alkyl-D-ribopyranoside is prepared by the reaction of 2-deoxy-D-ribose with alcohol in the presence of acid; (B) activation step in which 3 -and 4-OH groups of 2-deoxy-D-ribose are activated. 2-deoxy-l-O-alkyl- 3,4-di-(alkanesulfonyl)-D-ribose or 2-deoxy-1-O-alkyl-3,4-di-(arylsulfonyl)-D-ribose is prepared by reaction of the above 2-deoxy-l-O-alkyl-D-ribose with organic sulfonylhalide for activation of 3- and 4-OH; (C) inversion step in which stereochemistry of 3- and 4-OH groups is changed. Reaction of the above 2-deoxy-l- O-alkyl-3,4-di-(alkanesulfonyl)-D-ribose or 2-deoxy-l-O-alkyl-3,4-di-(arylsulfonyl)- D-ribose with a metal salt of organic acid leads to 2-deoxy-L-ribose derivatives of which stereochemistry of 3- and 4-OH is different from the corresponding 2-deoxy-D- ribose derivatives; (D) deprotection step in which 2-deoxy-L-ribose is prepared by consecutive reactions of the step (C) products with acid and base.
Purification Methods
Crystallise 2-deoxy--L-ribose from diethyl ether. It can also be purified by dissolving the ribose (7.3g) in EtOAc (3L) by reflux, decanting from any insoluble mate
