(+/-)-<(1,3/2,4,5)-5-acetamido-2,3,4-triacetoxycyclohexyl>-methyl acetate | 64589-26-0

• 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: (+/-)-<(1,3/2,4,5)-5-acetamido-2,3,4-triacetoxycyclohexyl>-methyl acetate
• 英文别名: DL-(1,3,4/2,6)-4-Acetamido-1,2,3-tri-O-acetyl-6-acetoxymethyl-1,2,3-cyclohexanetriol；Penta-N,O-acetyl-(+/-)-validamine；penta-N,O-acetyl-D,L-validamine；penta-N,O-acetyl-DL-validamine；(+/-)-validamine pentaacetate；peracetyl-DL-validamine
• CAS: 64589-26-0；68108-50-9；73651-28-2；74561-05-0；87038-27-5；108866-25-7；132342-13-3
• 化学式: C₁₇H₂₅NO₉
• 分子量: 387.387
• InChiKey: KOOWXFYUPXIRQJ-DMRKSPOLSA-N

物化性质

• 沸点：
  492.8±34.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  134.3
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (+/-)-<(1,3/2,4,5)-5-acetamido-2,3,4-triacetoxycyclohexyl>-methyl acetate 在 盐酸 、 sodium hydroxide 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 DL-3,4-N,O-carbonyl-1,7-O-isopropylidene-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol
  参考文献：
  名称：

  β-D-GLUCOPYRANOSYLVALIDAMINE 的合成：2-O-β-D-GLUCOPYRANOSYL-1L-(1,3,4/2,6)-4-AMINO-6-Hydroxymethyl-1,2,3-Cyclohexanetriol

  摘要：

  β-D-吡喃葡萄糖基有效胺 (1a)，其结构归属于有效霉素 A 的降解产物，通过受保护的有效胺 (8) 与乙酰溴葡萄糖缩合，然后解封来合成。出乎意料的是，发现 1a 与来自抗生素的真实样本不同。

  DOI：

  10.1246/cl.1980.135
• 作为产物：
  描述：

  (1S)-2-exo,3-endo-diacetoxy-5-endo-acetoxymethyl-7-oxabicyclo<2.2.1.>heptane 在 氢溴酸 作用下， 生成 (+/-)-<(1,3/2,4,5)-5-acetamido-2,3,4-triacetoxycyclohexyl>-methyl acetate
  参考文献：
  名称：

  Pseudo-sugars. 4. A Facile Synthesis of DL-Validamine and Its Derivative

  摘要：

  五-N,O-乙酰基-D1-有效胺由容易获得的内-2,外-3-二乙酰氧基-内-6-乙酰氧基甲基-7-氧杂二环[2.2.1]庚烷分三步制备，总产率为36 %。

  DOI：

  10.1246/bcsj.52.1174

文献信息

• Synthesis of a carba-sugar analog of trehalosamine, [(1S)-(1,2,43,5)-2-amino-3,4-dihydroxy-5-hydroxymethyl-1-cyclohexyl] α-d-glucopyranoside, and a revised synthesis of its β anomer
  作者：Seiichiro Ogawa、Kenji Nishi、Yasushi Shibata

  DOI：10.1016/0008-6215(90)80074-d

  日期：1990.10

  The synthesis of α-D-glucosides was performed by condensation of the newly prepared 3,4,7-tri-O-benzyl-2-deoxy-2-p-toluenesulfonamido-5a-carba-α-DL-glucopyranose with 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranose 2 in the presence of trimethylsilyl trifluoromethanesulfonate

  α-D-葡萄糖苷的合成是通过将新制备的3,4,7-三-O-苄基-2-脱氧-2-对甲苯磺酰氨基-5a-卡巴-α-DL-吡喃葡萄糖与1缩合而进行的在三甲基甲硅烷基三氟甲磺酸酯存在下的6-二-O-乙酰基-2,3,4-三-O-苄基-β-D-吡喃葡萄糖2
• SYNTHESIS OF 1-<i>O</i>-β-D-GLUCOPYRANOSYL-1L-(1,3,4/2,6)-4-AMINO-6-HYDROXYMETHYL-1,2,3-CYCLOHEXANETRIOL. ON THE STRUCTURE OF THE ANTIBIOTIC, VALIDAMYCIN A
  作者：Seiichiro Ogawa、Noritaka Chida、Tetsuo Suami

  DOI：10.1246/cl.1980.139

  日期：1980.2.5

  1-O-β-D-Glucopyranosyl-1L-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol (12) was synthesized and found to be identical with β-D-glucopyranosyl-validamine derived from validamycin A. The position at which validamine moiety was substituted with D-glucopyranose was revised to C-l on the basis of the present synthesis.

  合成了 1-O-β-D-吡喃葡萄糖基-1L-(1,3,4/2,6)-4-氨基-6-羟甲基-1,2,3-环己三醇 (12) 并发现与源自validamycin A的β-D-吡喃葡萄糖基-validamine。在本合成的基础上，将validamine部分被D-吡喃葡萄糖取代的位置修改为Cl。
• Synthetic Studies on the Validamycins. I. Synthesis of β-D-Glucopyranosylvalidamine: 1L-2-<i>O</i>-(β-D-Glucopyranosyl)-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol
  作者：Seiichiro Ogawa、Yasuhito Shibata、Noritaka Chida、Tetsuo Suami

  DOI：10.1246/bcsj.56.494

  日期：1983.2

  β-D-Glucopyranosylvalidamine, the structure of which had first been assigned to a degradation product of validamycin A, was synthesized by condensation of a protected validamine with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, followed by removal of protecting groups. The synthesized β-D-glucopyranoside was not identical with an authentic sample derived from the antibiotic.

  β-D-吡喃葡萄糖基有效胺，其结构首先被指定为有效霉素 A 的降解产物，通过受保护的有效胺与 2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基缩合合成溴，然后去除保护基团。合成的 β-D-吡喃葡萄糖苷与源自抗生素的真实样品不同。
• Total Synthesis of (±)-2-epi-Validamine
  作者：Hiroaki Okamura、Hiroshi Nagaike、Nsiama Tienabe Kipassa、Tetsuo Iwagawa、Munehiro Nakatani

  DOI：10.3987/com-06-10887

  日期：——

  (+/-)-Validamine and its epimers, (+/-)-2-epi-validamine (DL-5a-carba-alpha-mannopyranosylamine) and (+/-)-2-epi-3-epi-validamine (DL-5a-carba-alpha-altropyranosylamine) were synthesized from a poly-functionalized bicyclolactam that obtained by a base-catalyzed Diels-Alder reaction of N-tosyl-3-hydroxy-2-pyridone and methyl acrylate. All isomers were prepared via a common key intermediate in six or seven steps.

  (±)-Validamine及其表异构体，即(±)-2-表-validamine（DL-5a-羧甲基-α-D-吡喃甘露糖基胺）和(±)-2-表-3-表-validamine（DL-5a-羧甲基-α-D-吡喃艾利糖基胺），是由一个通过碱催化的N-甲苯磺酰基-3-羟基-2-吡啶酮与丙烯酸甲酯的Diels-Alder反应得到的多官能团环状酰胺合成的。所有异构体都是通过一个共同的键中间体在六到七步反应中制备完成的。
• Pseudo-sugars. 3. Alternative Synthesis of Penta-<i>N</i>,<i>O</i>-acetyl-DL-validamine and Its Analogs
  作者：Seiichiro Ogawa、Isamu Kasahara、Tetsuo Suami

  DOI：10.1246/bcsj.52.118

  日期：1979.1

  Dl-Validamine and its amino deoxy and deoxy analogs were synthesized as the acetyl derivatives from endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, the Diels-Alder adduct of acrylic acid and furan.

  Dl-Validamine及其氨基脱氧和脱氧类似物是从内-7-氧杂双环[2.2.1]庚-5-烯-2-羧酸（丙烯酸和呋喃的Diels-Alder加合物）合成的乙酰衍生物。