The Reactions of β-and α-Pyranose Peracetates with PCl_5,and Utilization of the Products to Construct Sarsasapogenin Glycosides

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概要

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• The reactions of β-and α-pyranose with PCl_5 gave products regioselectively chlorinated. The reactions of 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (5) and -β-D-galactopyranose (6) with PCl_5 in CCl_4 and that of methyl 2,3,4-tri-O-acetyl-β-D-glucuranatopyranose (7) with PCl_5 in toluene gave 2-O-trichloroacetyl-β-D-pyranosyl chlorides 4,12 and 14,respectively, as major products, and α-D-pyranosyl chlorides 11,13 and 15,respectively, as minor products. On the other hand, the reactions of compounds 8 and 9 which were α-anomers of 5 and 6,respectively, with PCl_5 gave as major products transformed acetyl groups at C-6 to -C(Cl)=CCl_2 or -C(Cl)_2-CCl_3 group (16 and 17 from 8 and 18 from 9). The same reaction of 10,which was α-anomer of 7,gave α-chloride 15 as major product. The glycosidation of sugar derivative 4 with sarsasapogenin 23 gave β-glycoside 24 (29.1%) and α-glycosides 25 (46.9%), and that of 12 with 23 gave β-glycoside 26 (24.0%) and α-glycoside 27 (40.8%). The improvement of the yields of β-glycosides 24 and 26 (66.9 and 62.1% for 24 and 26,respecitvely) in the glycosidations were accomplished by the employment of α-bromides 28 and 29 obtained from 4 and 6,respectively. The glycosidations of monoglycosides 30 and 31 obtained by the treatment 24 and 26,respectively, with ammonia-saturated ether with sugar acetate bromides 32 and 34 gave diglycoside derivatives 35 and 33,respectively.

• 社団法人日本薬学会の論文
• 1992-12-25

著者

• 斎藤 節生

  Faculty of Pharmaceutical Sciences, Josai University

• 角田 繁也

  Shiratori Pharmaceutical Co., Ltd.

• 佐々木 由佳

  Faculty of Pharmaceutical Sciences, Josai University

• 佐々木 由佳

  Faculty Of Pharmaceutical Sciences Josai University

• 斎藤 節生

  Faculty Of Pharmaceutical Sciences Josai University

• 一ノ瀬 公樹

  Faculty of Pharmaceutical Sciences, Josai University

• 角田 繁也

  Shiratori Pharmaceutical Co. Ltd.

• 一ノ瀬 公樹

  Faculty Of Pharmaceutical Sciences Josai University

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