di-O-acetyl-2-deoxy-D-erythro-pentopyranosyl chloride | 68323-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: di-O-acetyl-2-deoxy-D-erythro-pentopyranosyl chloride
• 英文别名: 2-Desoxy-acetochlor-ribopyranose；3,4-Di-O-acetyl-2-deoxy-D-ribopyranosyl chloride；2-deoxy-3,4-di-0-acetyl-D-erythro-pentapyranosyl chloride；[(4S,5R)-5-acetyloxy-2-chlorooxan-4-yl] acetate
• CAS: 68323-15-9
• 化学式: C₉H₁₃ClO₅
• 分子量: 236.652
• InChiKey: WFUDUMBRJHQZAI-ZQTLJVIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  di-O-acetyl-2-deoxy-D-erythro-pentopyranosyl chloride 在 sodium hydroxide 、 4 A molecular sieve 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 甲醇 为溶剂， 反应 26.17h， 生成 10-O-(6-carboxyhexanoyl)-7-O-(2'-deoxy-β-D-erythro-pentopyranosyl)-β-rhodomycinone
  参考文献：
  名称：

  Kita, Yasuyuki; Maeda, Hiroshi; Takahashi, Fumie, Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2639 - 2650

  摘要：

  DOI：

文献信息

• Total synthesis of 11-deoxyanthracyclines: 4-Demethoxy-11-deoxydaunomycin, 11-deoxydaunomycin, and their analogues.
  作者：YASUMITSU TAMURA、SHUJI AKAI、HISAKAZU KISHIMOTO、MANABU SASHO、MASAYUKI KIRIHARA、YASUYUKI KITA

  DOI：10.1248/cpb.36.3897

  日期：——

  Practical total synthesis of 11-deoxyanthracyclinones (8 and 9) was accomplished on the basis of two effective syntheses of the key intermediates (14 and 15) and the subsequent highly stereoselective introduction of a C-7 cis-hydroxyl group. Glycosidation of 8 with a suitably protected L-daunosamine (37) followed by deprotection provided 4-demethoxy-11-deoxydaunomycin (5). The C-13 acetal derivative (34) of 9 was successfully employed for the glycosidation to achieve the first total synthesis of 11-deoxydaunomycin (6). Two novel synthetic 11-deoxyanthracyclines (10 and 11) possessing a neutral sugar instead of L-daunosamine were also synthesized.

  基于两个有效的关键中间体（14和15）的合成方法，以及随后高度立体选择性引入C-7顺式羟基，成功实现了11-脱氧蒽环酮（8和9）的实用全面合成。将8与适当保护的L-道诺沙敏（37）进行糖苷化，随后去保护，得到4-去甲氧基-11-脱氧道诺霉素（5）。9的C-13乙缩醛衍生物（34）成功用于糖苷化，从而实现了11-脱氧道诺霉素（6）的首次全面合成。此外，还合成了两种新型的11-脱氧蒽环素（10和11），它们以中性糖取代了L-道诺沙敏。
• Aminonaphthacene derivatives
  申请人：Sumitomo Pharmaceuticals Company

  公开号：US04673668A1

  公开（公告）日：1987-06-16

  9-Aminonaphthacene derivative having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are both hydrogen atoms or either one of them is a hydrogen atom and the other is hydroxy group or methoxy group; R.sup.3 is acetyl group or 1-hydroxyethyl group; R.sup.4 is a hydrogen atom; R.sup.5 is a hydrogen atom, hydroxy group, lower alkanoyloxy group, amino group, halogen-substituted lower alkanoylamino group or morpholino group; R.sup.6 is a hydrogen atom, hydroxy group, lower alkanoyloxy group or tetrahydropyranyloxy group; R.sup.7 is a hydrogen atom or methyl group; R is a hydrogen atom; and n is zero or one, which is useful as anti-cancer chemical agents with lower toxicity and with little local irritation and is able to orally be applied.

  具有以下式子的9-氨基萘啶衍生物：##STR1## 其中R.sup.1和R.sup.2都是氢原子，或者其中一个是氢原子，另一个是羟基或甲氧基；R.sup.3是乙酰基或1-羟乙基基团；R.sup.4是氢原子；R.sup.5是氢原子、羟基、较低的烷酰氧基团、氨基、卤代较低的烷酰胺基团或吗啡环基团；R.sup.6是氢原子、羟基、较低的烷酰氧基团或四氢吡喃氧基团；R.sup.7是氢原子或甲基基团；R是氢原子；n为零或一。该化合物是一种抗癌化学药剂，具有较低的毒性和较少的局部刺激，并且可以口服应用。
• Synthesis of 2'-deoxy-L-fucopyranosylcarminomycinone and -.epsilon.-pyrromycinone as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -.epsilon.-pyrromycinone
  作者：Hassan S. El Khadem、David L. Swartz

  DOI：10.1021/jm00133a023

  日期：1981.1

  Treatment of di-O-acetyl-2-deoxy-L-fucopyranosyl bromide with carminomycinone and epsilon-pyrromycinone in the presence of mercuric bromide and mercuric cyanide afforded 3',4'-diO-acetyl-2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone. Similarly, when di-O-acetyl-2-deoxy-D-erythrho-pentopyranosyl chloride was treated with daunomycinone, carminomycinone and epsilon-pyrromycinone, the di-O-acetyl derivatives of the anthracyclinone glycosides were obtained. Deacetylation of the previous acetates with sodium methoxide afforded 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone, as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone. 2'-Deoxy-L-fucopyranosylcarminomycinone was found to be more active than carminomycin at higher dosages on L1210.
• TAMURA, YASUMITSU;AKAI, SHUJI;KISHIMOTO, HISAKAZU;SASHO, MANABU;KIRIHARA,+, CHEM. AND PHARM. BULL., 36,(1988) N 10, C. 3897-3914
  作者：TAMURA, YASUMITSU、AKAI, SHUJI、KISHIMOTO, HISAKAZU、SASHO, MANABU、KIRIHARA,+

  DOI：——

  日期：——
• US3996205A
  申请人：——

  公开号：US3996205A

  公开（公告）日：1976-12-07