Benzyl 2,3,4-Tri-O-acetyl-α-D-arabinopyranoside | 151557-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 2,3,4-Tri-O-acetyl-α-D-arabinopyranoside
• 英文别名: benzyl-(tri-O-acetyl-α-D-arabinopyranoside)；Benzyl-(tri-O-acetyl-α-D-arabinopyranosid)；[(3R,4R,5S,6S)-4,5-diacetyloxy-6-phenylmethoxyoxan-3-yl] acetate
• CAS: 151557-73-2
• 化学式: C₁₈H₂₂O₈
• 分子量: 366.368
• InChiKey: LHFOAGYPATWZGW-BDXSIMOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Benzyl 2,3,4-Tri-O-acetyl-α-D-arabinopyranoside 在 sodium periodate 、 sodium methylate 、 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 1,5-dihydroxy-2(S)-benzyloxy-3-oxapentane
  参考文献：
  名称：

  ANTHRACYCLINS AND CONJUGATES THEREOF

  摘要：

  The invention concerns analogues of nemorubicin as well as PNU-159,682 with a range of substituents other than 2"-0Me on the morpholino ring that beneficially affected the toxicity of the toxin over the molecules with the 2"-0Me group. In addition, it was found that PNU variants with modified 2"-O-alkyl chain show enhanced tolerability in vivo. Thus, by modification of the 2"-O-alkyl group, ADCs were generated with carefully tailored potency and tolerability to improve the administered dose in patients. The invention thus concerns compounds according to structure (1) and conjugates therewith, as well as pharmaceutical compositions and methods of targeting tumour cells and treating cancer.

  公开号：

  WO2024038065A1
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-β-D-arabinopyranose 在 氢溴酸 、 乙酸酐 、 溶剂黄146 、 silver(l) oxide 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 Benzyl 2,3,4-Tri-O-acetyl-α-D-arabinopyranoside
  参考文献：
  名称：

  ANTHRACYCLINS AND CONJUGATES THEREOF

  摘要：

  The invention concerns analogues of nemorubicin as well as PNU-159,682 with a range of substituents other than 2"-0Me on the morpholino ring that beneficially affected the toxicity of the toxin over the molecules with the 2"-0Me group. In addition, it was found that PNU variants with modified 2"-O-alkyl chain show enhanced tolerability in vivo. Thus, by modification of the 2"-O-alkyl group, ADCs were generated with carefully tailored potency and tolerability to improve the administered dose in patients. The invention thus concerns compounds according to structure (1) and conjugates therewith, as well as pharmaceutical compositions and methods of targeting tumour cells and treating cancer.

  公开号：

  WO2024038065A1

文献信息

• Klotz, Wolfgang; Schmidt, Richard R., Liebigs Annalen der Chemie, 1993, # 6, p. 683 - 690
  作者：Klotz, Wolfgang、Schmidt, Richard R.

  DOI：——

  日期：——
• Reductive Cleavage of Benzyl Glycosides for Relating Anomeric Configurations. Preparation of Some New Benzyl Pentosides¹
  作者：Clinton E. Ballou、Saul Roseman、Karl Paul Link

  DOI：10.1021/ja01147a076

  日期：1951.3
• Regioselective and stereoselective oxirane ring-openings of 2,3-anhydropentopyranosides with some methyl-group donating organometallic reagents
  作者：Tord Inghardt、Torbjoern Frejd、Goeran Magnusson

  DOI：10.1021/jo00254a023

  日期：1988.9