D-2,3;4,5-di-O-cyclohexylidene-6-deoxy-myo-inositol | 228562-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-2,3;4,5-di-O-cyclohexylidene-6-deoxy-myo-inositol
• 英文别名: 2,3:4,5-di-O-cyclohexylidene-(+)-epi-quercitol
• CAS: 228562-73-0
• 化学式: C₁₈H₂₈O₅
• 分子量: 324.417
• InChiKey: RYCIQSISIBVGIX-QRJUGERDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-2,3;4,5-di-O-cyclohexylidene-6-deoxy-myo-inositol 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 D-2,3;4,5-di-O-cyclohexylidene-6-deoxy-myo-inositol-1-(dibenzyl)phosphate
  参考文献：
  名称：

  Stereoselective synthesis of inositol mono, bis and trisphosphate analogues from 6-deoxy- d -inositol precursors

  摘要：

  The synthesis of opticaly pure deoxy-myo-inositol mono, bis and trisphosphate analogues is described from 4-O-benzyl-2,3-di-O-cyclohexylidene-6-deoxy-myo-inositol and corresponding 1,5 epimer chiro-inositol. These precursors, which derive from galactose, are used to accede to a variety of cyclitol intermediates employing protection/deprotection sequence. The phosphorylation procedure was performed to produce free and original substituted phosphate derivatives aimed to be incorporated through the lipidic cell membrane for in vivo evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00365-8
• 作为产物：
  描述：

  以61%的产率得到
  参考文献：
  名称：

  BAKER, RAYMOND;KULAGOWSKI, JANUSZ J.;BILLINGTON, DAVID C.;LEESON, PAUL D.+, J. CHEM. SOC. CHEM. COMMUN.,(1989) N8, C. 1383-1385

  摘要：

  DOI：

文献信息

• SYNTHESIS OF 1- AND 3-C-(AMINOMETHYL)-1,2,3,4,5-CYCLOHEXANEPENTOLS FROM (+)-epi-QUERCITOL1
  作者：Seiichiro Ogawa、Hiroshi Aoyama、Yoji Tezuka

  DOI：10.1081/car-100108284

  日期：——

  Oxidation of three di-O-isopropylidene derivatives 2a-4a, newly derived from (+)-epi-quercitol (1), with acetic anhydride in DMSO gave the corresponding ketones 5-7, which underwent aldol-type condensation with nitromethane under basic conditions to give selectively the protected derivatives 8a-10a of C-nitromethyl-1,2,3,4,5-cyclohexanepentols, respectively. On treatment with diazomethane in DMSO, the ketones 6 and 7 gave single spiro epoxides 11 and 12, the structures of which were confirmed by converting them into new C-(azidomethyl)cyclohexanepentols 16 and 17. The nitro compounds were hydrogenated in the presence of Raney nickel to give the amines isolated as the N-acetyl derivatives. Deprotection gave three new 1- and 3-C-aminomethyldeoxyinositols 15c-17c. The aminocyclitols obtained and their N-acetyl derivatives were assayed for inhibitory activity against examples of glycosidases.