2,3,4,6-tetra-O-isobutyryl-α-D-glucopyranosyl bromide | 119607-30-6

• 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: 2,3,4,6-tetra-O-isobutyryl-α-D-glucopyranosyl bromide
• 英文别名: [(2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]methyl 2-methylpropanoate
• CAS: 119607-30-6
• 化学式: C₂₂H₃₅BrO₉
• 分子量: 523.418
• InChiKey: VKDDXNLVMHFZPD-SFFUCWETSA-N

物化性质

• 沸点：
  498.5±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-isobutyryl-α-D-glucopyranosyl bromide 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 氢氟酸 、 silver trifluoromethanesulfonate 作用下， 以 1,4-二氧六环 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 18.17h， 生成 (-)-(1Z)-{(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2,3,4,6-tetra-O-isobutyryl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-yliden}acetonitrile
  参考文献：
  名称：

  Total Synthesis of (−)-Bauhinin

  摘要：

  The total synthesis of the naturally occurring cyanoglucoside (-)-bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (-)-bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig-Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra-O-isobutyryl-D-glucosyl bromide 9 as the reagent in the Koenigs-Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (-)-bauhinin (1).

  DOI：

  10.1002/1522-2675(20010418)84:4<890::aid-hlca890>3.0.co;2-q
• 作为产物：
  描述：

  1,2,3,4,6-penta-O-isobutyryl-D-glucopyranose 在 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 14.0h， 以82%的产率得到2,3,4,6-tetra-O-isobutyryl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  受阻醇的β-D-葡萄糖苷的选择性形成

  摘要：

  Koenigs-Knorr 经典糖苷化方法的替代条件使我们能够在弱酸性到几乎中性的介质中以高产率选择性地制备几种受阻醇的 β-D-葡萄糖苷。为了说明我们条件的多功能性，我们制备了酸敏感苷元的 β-D-葡糖苷，这是全合成天然氰基葡糖苷紫荆苷的关键中间体。

  DOI：

  10.1002/1522-2675(20010418)84:4<880::aid-hlca880>3.0.co;2-u

文献信息

• Total Synthesis of (2Z)-[(4R,5R,6S)-6-(β-D-Glucopyranosyloxy)-4,5-dihydroxycyclohex-2-en-1-ylidene]ethanenitrile, a Cyanoglucoside fromIlex warburgii
  作者：Delphine Josien-Lefebvre、Claude Le Drian

  DOI：10.1002/hlca.200790015

  日期：2007.1

  The total synthesis of the noncyanogenic cyanoglucoside 1, originally isolated from Ilex warburgii, was achieved in nine steps (9% overall yield), starting from an optically pure Diels–Alder adduct ((+)-3). The key step of the synthesis, the glycosidation, was carried out under Koenigs–Knorr conditions closely related to those developed for the total syntheses of (−)-lithospermoside and (−)-bauhinin

  从光学纯的Diels–Alder加合物（（+）- 3）开始，九个步骤（总收率为9％）实现了最初从华氏冬青属植物中分离出来的非氰基氰基葡萄糖苷1的总合成。合成的关键步骤，糖基化，是在Koenigs-Knorr条件下进行的，该条件与为（-）-紫草精苷和（-）-紫胶苷的总合成开发的条件紧密相关。我们必须调节用于糖苷配基的两个自由的顺式构型的OH基的保护基，其以非常好的收率（62％）提供了所需的β -d-葡糖苷中间体15。
• Colchinol derivatives as vascular damaging agents
  申请人：Davis D. Peter

  公开号：US20060128633A1

  公开（公告）日：2006-06-15

  The invention relates to the use of compounds of formula (I): wherein X is —C(O)—, —C(S)—, —C═NOH, or —CH(R 7 )— wherein R 7 is hydrogen, hydroxy, C 1-7 alkoxy, —OR 8 or —NR 8 R 9 (wherein R 8 is a group —Y 1 R 10 (wherein Y 1 is a direct bond, —C(O)—, —C(S)—, —S—, —C(O)O—, —C(O)NR 11 —, —SO 2 — or —SO 2 NR 12 — (wherein R 11 and R 12 , which may be the same or different, each independently represents hydrogen; C 1-3 alkyl or C 1-3 alkoxyC 2-3 alkyl) and R 10 is as defined herein, R 9 includes hydrogen; R 11 , R 12 and R 13 are as defined herein and are preferably methyl; R 4 , R 5 and R 6 are as defined herein with the proviso that R 5 is not hydroxy, alkoxy, substituted alkoxy, —OPO 3 H 2 , —O—C 1-7 alkanoyl or benzyloxy; and salts thereof in the manufacture of a medicament for use in the production of a vascular damaging effect in warm-blooded animals such as humans. The present invention further relates to compounds of the formula (I), pharmaceutical compositions containing them, processes for their preparation and to a method of treatment using the compounds to produce a vascular damaging effect in a warm-blooded animal such as a human. The compounds of formula (I) and the pharmaceutically acceptable salts thereof may be useful in the treatment of a number of disease states including cancer and rheumatoid arthritis.

  本发明涉及使用以下化合物（I）的制药用途：其中X为—C（O）—、—C（S）—、—C═NOH或—CH（R7）—，其中R7为氢、羟基、C1-7烷氧基、—OR8或—NR8R9（其中R8为—Y1R10基团，其中Y1为直接键、—C（O）—、—C（S）—、—S—、—C（O）O—、—C（O）NR11—、—SO2—或—SO2NR12—（其中R11和R12，可以相同也可以不同，各自独立地表示氢、C1-3烷基或C1-3烷氧基C2-3烷基），而R10如上所述，R9包括氢；R11、R12和R13如上所述，且最好为甲基；R4、R5和R6如上所述，但其中R5不是羟基、烷氧基、取代烷氧基、—OPO3H2、—O—C1-7烷酰基或苄氧基；以及它们的盐在制造用于在温血动物如人类中产生血管损伤效应的药物中的应用。本发明还涉及化合物（I）、含有它们的制药组合物、其制备方法以及使用这些化合物在温血动物如人类中产生血管损伤效应的治疗方法。化合物（I）及其药学上可接受的盐可以在治疗包括癌症和类风湿性关节炎在内的多种疾病状态中有用。
• COLCHINOL DERIVATIVES AS VASCULAR DAMAGING AGENTS
  申请人：Angiogene Pharmaceuticals Ltd

  公开号：EP1140745B1

  公开（公告）日：2003-10-22
• Brown, Richard T.; Fox, Brian W.; Hadfield, John A., Journal of the Chemical Society. Perkin transactions I, 1995, # 5, p. 577 - 582
  作者：Brown, Richard T.、Fox, Brian W.、Hadfield, John A.、McGown, Alan T.、Mayalarp, Stephen P.、et al.

  DOI：——

  日期：——
• US7135502B1
  申请人：——

  公开号：US7135502B1

  公开（公告）日：2006-11-14