3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-mannopyranosyl chloride | 72864-45-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-mannopyranosyl chloride
• 英文别名: 3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-glucopyranosyl chloride；3,4-di-O-acetyl-2-chloro-2,6-dideoxy-β-L-glucopyranosyl chloride；3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-galactopyranosyl chloride；3,4-di-O-acetyl-2-chloro-2,6-dideoxy-β-L-talopyranosyl chloride；3,4-di-O-acetyl-2-chloro-2,6-dideoxy-β-L-galactopyranosyl chloride；3,4-di-O-acetyl-2-chloro-2,6-dideoxy-β-L-mannopyranosyl chloride
• CAS: 72864-45-0；103321-18-2；103321-19-3；103321-20-6；103321-21-7；103321-23-9；103321-24-0；104068-99-7
• 化学式: C₁₀H₁₄Cl₂O₅
• 分子量: 285.124
• InChiKey: FBIFULIAMTVFMQ-YYZGGASCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  柔红酮 、 3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-mannopyranosyl chloride 在 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 以44%的产率得到7-O-(3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-galactopyranosyl)daunomycinone
  参考文献：
  名称：

  Synthesis and antitumor activity of 2′-bromo- and 2′-chloro-3′-acetoxy-3′-deaminodaunorubicin analogs

  摘要：

  Bromination of 3,4-di-O-acetyl-L-rhamnal (7) and subsequent glycosidic coupling under Koenigs-Knorr conditions with daunomycinone gave a mixture of three compounds having the beta-L-gluco (10), alpha-L-gluco (11), and alpha-L-manno (12) configurations. Analogous bromination of 3,4-di-O-acetyl-L-fucal (13) followed by coupling with daunomycinone gave a mixture of three glycosides having the beta-L-galacto (16), alpha-L-galacto (17), and alpha-L-talo (18) configurations. Chlorination of 7 and coupling with daunomycinone in the presence of silver triflate gave products having the alpha-L-gluco (21) and alpha-L-manno (22) configurations, whereas 13, under similar conditions, gave only one stereoisomeric product, that having the alpha-L-galacto (24) configuration. Compounds 12 and 22 showed high in vivo activity in the P-388 lymphocytic leukemia assay.

  DOI：

  10.1016/s0008-6215(00)90678-5
• 作为产物：
  描述：

  2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 氯 作用下， 以 四氯化碳 为溶剂， 反应 0.17h， 生成 3,4-di-O-acetyl-2-chloro-2,6-dideoxy-α-L-mannopyranosyl chloride
  参考文献：
  名称：

  Synthesis and antitumor activity of 2′-bromo- and 2′-chloro-3′-acetoxy-3′-deaminodaunorubicin analogs

  摘要：

  Bromination of 3,4-di-O-acetyl-L-rhamnal (7) and subsequent glycosidic coupling under Koenigs-Knorr conditions with daunomycinone gave a mixture of three compounds having the beta-L-gluco (10), alpha-L-gluco (11), and alpha-L-manno (12) configurations. Analogous bromination of 3,4-di-O-acetyl-L-fucal (13) followed by coupling with daunomycinone gave a mixture of three glycosides having the beta-L-galacto (16), alpha-L-galacto (17), and alpha-L-talo (18) configurations. Chlorination of 7 and coupling with daunomycinone in the presence of silver triflate gave products having the alpha-L-gluco (21) and alpha-L-manno (22) configurations, whereas 13, under similar conditions, gave only one stereoisomeric product, that having the alpha-L-galacto (24) configuration. Compounds 12 and 22 showed high in vivo activity in the P-388 lymphocytic leukemia assay.

  DOI：

  10.1016/s0008-6215(00)90678-5