2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol | 75499-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol
• 英文别名: 2,5-anhydro-4,6-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol；[(4aS,6R,7R,7aR)-7-benzoyloxy-2,2-dimethyl-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-6-yl]methyl benzoate
• CAS: 75499-82-0
• 化学式: C₂₃H₂₄O₇
• 分子量: 412.439
• InChiKey: VEVTXBCHDVXHON-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以97.4%的产率得到2,5-anhydro-1,3-O-isopropylidene-D-glucitol
  参考文献：
  名称：

  Intermediate compounds in the synthesis of the A ring moiety of 2-substituted vitamin D derivatives

  摘要：

  本发明的目的是提供一种新型化合物，其对应于具有2-位置取代基的维生素D衍生物的A环部分。根据本发明，提供了通式（1）的化合物：（其中R1、R2和R3，可以相同也可以不同，表示氢原子或保护基，而R4表示较低的烷基），用于合成它们的中间体以及制备它们的方法。

  公开号：

  US06335458B1
• 作为产物：
  描述：

  2,5-脱水-D-葡萄糖醇 在 硫酸 作用下， 以 吡啶 、 丙酮 为溶剂， 生成 2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol
  参考文献：
  名称：

  Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

  摘要：

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00069-5

文献信息

• D-Arbinose-Based Synthesis of homo-<i>C</i>-d4T and homo-<i>C</i>-thymidine
  作者：Bogdan Doboszewski

  DOI：10.1080/15257770903306518

  日期：2009.10.28

  2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. D-Arbinose-Based Synthesis of homo-C-d4T and homo-C-thymidineAll authorsBogdan Doboszewskihttps://doi.org/10.1080/15257770903306518 Published online:20 October 2009

  使2,3,5-Tri- O-苄基-D-阿拉伯呋喃糖基卤化物（氯化物，溴化物）与AllMgBr，MeMgBr和VinMgBr反应，以提供C-糖基产物的异头混合物。讨论了影响β/α比的因素。将α，β- C-乙烯基衍生物转化为1-脱氧-1- C-羟甲基-β-和-α-D-阿拉伯呋喃糖酶（分别为2,5-脱水-D-葡萄糖醇和-甘露醇），可在分离后分离异丙基化步骤。2,5-脱水-1,3- O-异亚丙基-D-葡萄糖醇被转化为2,5-脱水-6- O-三苯甲基-D-赤型-hex-3,4-烯醇和2,5-脱水- 4,6-二-O-苯甲酰基-3-脱氧-D-核糖-己糖醇，在Mitsunobu条件下与N-3-苯甲酰胸腺嘧啶偶联，以提供两个在糖基团和胸腺嘧啶之间插入-CH 2-的核苷类似物。 的d-Arbinose基于合成均聚物Ç -d4T和均聚Ç -胸苷所有作者Bogdan Doboszewski https://doi
• INTERMEDIATE COMPOUNDS IN THE SYNTHESIS OF THE A RING MOIETY OF 2-SUBSTITUTED VITAMIN D DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1072582A1

  公开（公告）日：2001-01-31

  The object of the present invention is to provide novel compounds corresponding to the A ring part of vitamin D derivatives having a substituent at the 2-position. According to the present invention, there are provided compounds of the general formula (1): (wherein R1, R2 and R3, which may be the same or different, represent a hydrogen atom or a protecting group and R4 represents a lower alkyl group), intermediates for synthesizing them and a process for preparing them.

  本发明的目的是提供与维生素 D 衍生物的 A 环部分相对应的新型化合物，该化合物在 2 位上具有取代基。根据本发明，提供了通式（1）的化合物： (其中 R1、R2 和 R3（可以相同或不同）代表氢原子或保护基，R4 代表低级烷基）、合成它们的中间体和制备它们的工艺。
• Synthesis of Homo-C-D4T and Homo-C-Thymidine
  作者：Bogdan Doboszewski

  DOI：10.1080/07328319708006130

  日期：1997.7

  beta-C-Vinyl glycoside of D-arabinofuranose was converted to the beta-C-hydroxymethyl glycoside 12 which was condensed with N-3-benzoyl thymine under Mitsunobu conditions to furnish homo-C-analog 14 of the 2',3'-dideoxy-2',3'-didehydrothymidine (D4T). Synthesis of the homo-C-thymidine 18 was accomplished by the same procedure from compound 15.
• Mubarak, Azeez M.; Brown, Daniel M., Journal of the Chemical Society. Perkin transactions I, 1982, p. 809 - 814
  作者：Mubarak, Azeez M.、Brown, Daniel M.

  DOI：——

  日期：——
• US6335458B1
  申请人：——

  公开号：US6335458B1

  公开（公告）日：2002-01-01