tetra-O-benzyl-1-epivalienamine | 128573-02-4

• 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: tetra-O-benzyl-1-epivalienamine
• 英文别名: (1R,4R,5S,6S)-4,5,6-tris(phenylmethoxy)-3-(phenylmethoxymethyl)cyclohex-2-en-1-amine
• CAS: 128573-02-4
• 化学式: C₃₅H₃₇NO₄
• 分子量: 535.683
• InChiKey: MDUAJXWOQSCPNG-WDKGQIBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tetra-O-benzyl-1-epivalienamine 生成 (1S,2R,3R,6R)-6-amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
  参考文献：
  名称：

  NICOTRA, FRANCESCO;PANZA, LUIGI;RONCHETTI, FIAMMA;RUSSO, GIOVANNI, GAZZ. CHIM. ITAL., 119,(1989) N1, C. 577-579

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 在 四(三苯基膦)钯 、 sodium azide 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 tetra-O-benzyl-1-epivalienamine
  参考文献：
  名称：

  Nicotra, Francesco; Panza, Luigi; Ronchetti, Fiamma, Gazzetta Chimica Italiana, 1989, vol. 119, # 11, p. 577 - 580

  摘要：

  DOI：

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
• β-Acarbose. VII. Approaches Towards the Synthesis of Some N-Linked Carba-Oligosaccharides
  作者：Matthew G. Tilbrook、Robert V. Stick、Spencer J. Williams

  DOI：10.1071/ch99030

  日期：——

  3,4-Anhydro-1,6-dideoxy-1,6-episeleno-β-D-glucose was treated with cyclohexylamine to afford an amino diol which was subsequently converted into a cyclic carbamate, a compound shown to be a moderately successful glycosyl donor. Treatment of the same 3,4-anhydro sugar and the 1,6-epithio analogue with a 1-epivalienamine derivative afforded the corresponding secondary amines which were converted into the analogous cyclic carbamates. The epithio analogue was unsuccessful as a glycosyl donor, failing to glycosylate a carbohydrate alcohol. On the other hand, the episeleno compound appeared to function as a glycosyl donor but decomposition of the product occurred under the conditions necessary for its isolation.

  3,4-脱水-1,6-二脱氧-1,6-表硒-β-D-葡萄糖经环己基胺处理后，生成氨基二醇，随后转化为葡萄糖。 环己胺处理，得到氨基二醇，随后将其转化为环氨基甲酸酯。 环氨基甲酸酯。 供体。将相同的 3,4-anhydro 糖和 1,6-epithio 类似物 1-epivalienamine 衍生物处理后，可得到相应的仲胺 转化为类似的环氨基甲酸酯。表硫代 类似物作为糖基供体并不成功，未能糖基化碳水化合物醇。 碳水化合物醇。另一方面，表硒化合物似乎可以 但在其分离所需的条件下，产物会发生分解。 但在分离所需的条件下，产物发生了分解。
• β-Acarbose. VIII.The Synthesis of Some N-Linked Carba-Oligosaccharides
  作者：Matthew G. Tilbrook、Robert V. Stick、Spencer J. Williams

  DOI：10.1071/ch99031

  日期：——

  Two carbohydrate triflates have been used to alkylate a 1-epivalienamine derivative to give small amounts of the desired secondary amines, in addition to amounts of the products of elimination. Deprotection of the secondary amines afforded a carba-disaccharide and a carba-tetrasaccharide which have been shown to be good inhibitors of β-glucosidases.

  用两种碳水化合物三酸酯将 1-环戊二烯胺衍生物烷基化 衍生物进行烷基化，除得到少量所需的仲胺外 消除产物的数量。仲胺的脱保护 仲胺的脱保护作用可得到一种卡巴二糖和一种卡巴四糖。 这两种物质已被证明是 β-葡萄糖苷酶的良好抑制剂。
• An Investigation into the Synthesis of Some Molecules Related to Methyl Acarviosin
  作者：Matthew J. McDonough、Robert V. Stick、D. Matthew G. Tilbrook、Andrew G. Watts

  DOI：10.1071/ch03185

  日期：——

  Methyl acarviosin is an impressive inhibitor of some glycoside hydrolases that process substrates containing α-D-glucosidic linkages. In an attempt to provide putative inhibitors for enzymes that process β-D-glucosidic linkages, we report an improved synthesis of a hydroxylated ‘methyl β-acarviosin’ and our efforts towards various deoxygenated versions of methyl β-acarviosin. As well, the synthesis

  Methyl acarviosin 是一些糖苷水解酶的显着抑制剂，这些糖苷水解酶处理含有 α-D-糖苷键的底物。为了尝试为处理 β-D-糖苷键的酶提供推定的抑制剂，我们报告了羟基化的“甲基 β-acarviosin”的改进合成以及我们对各种脱氧形式的甲基 β-acarviosin 的努力。同样，报告了甲基 β-acarviosin 的 1,3-连接变体的合成，以及在 acarviosins 中构建关键氮键的不成功的“系链”方法。
• β-Acarbose. I The Synthesis of 1-Epivalienamine
  作者：Joseph C. McAuliffe、Robert V. Stick

  DOI：10.1071/c96151

  日期：——

  Improvements and modifications to a literature procedure for the synthesis of multigram amounts of a derivative of 1-epivalienamine are described. As well, various other derivatives of 1-epivalienamine, of potential use in the synthesis of carba sugars, are reported.

  本文介绍了对文献中合成多克量 1-epivalienamine 衍生物的方法的改进和修改。 多克 1-表戊二烯胺衍生物的改进和修改。以及 1-epivalienamine 的其他各种衍生物，这些衍生物可能用于 合成卡巴糖的潜在用途。