(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)piperidin-2-one | 158349-25-8

• 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: (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)piperidin-2-one
• 英文别名: (3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidin-2-one
• CAS: 158349-25-8
• 化学式: C₃₄H₃₅NO₅
• 分子量: 537.656
• InChiKey: ZXLUBBNCEANTCA-JDIHBLRXSA-N

物化性质

• 沸点：
  694.7±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)piperidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以71%的产率得到[2R-(2α,3α,4α,5β)]-3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]piperidine
  参考文献：
  名称：

  Dual-Action Lipophilic Iminosugar Improves Glycemic Control in Obese Rodents by Reduction of Visceral Glycosphingolipids and Buffering of Carbohydrate Assimilation

  摘要：

  The lipophilic iminosugar N-[5-(adamantan-1-ylmethoxy)pentyl]-1-deoxynojirimycin (2, AMP-DNM) potently controls hyperglycemia in obese rodent models of insulin resistance. The reduction of visceral glycosphingolipids by 2 is thought to underlie its beneficial action. It cannot, however, be excluded that concomitant inhibition of intestinal glycosidases and associated buffering of carbohydrate assimilation add to this. To firmly establish the mode of action or 2, we developed a panel of lipophilic iminosugars varying in configuration at C-4/C-5 and N-substitution of the iminosugar. From these we identified the L-ido derivative of 2, L-ido-AMP-DNM (4), as a selective inhibitor of glycosphingolipid synthesis. Compound 4 lowered visceral glycosphingolipids in ob/ob mice and ZDF rats on a par with 2. In contrast to 2, 4 did not inhibit sucrase activity or sucrose assimilation. Treatment with 4 was significantly less effective in reducing blood glucose and HbAlc. We conclude that the combination of reduction of glycosphingolipids in tissue and buffering of carbohydrate assimilation by 2 produces a superior glucose homeostasis.

  DOI：

  10.1021/jm901281m
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactonamide 在 ammonium hydroxide 、 乙酸酐 、 sodium cyanoborohydride 、 二甲基亚砜 作用下， 以 甲酸 、 乙腈 为溶剂， 反应 14.0h， 生成 (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)piperidin-2-one
  参考文献：
  名称：

  A facile transformation of sugar lactones to azasugars

  摘要：

  The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.

  DOI：

  10.1016/s0040-4020(01)86715-6

文献信息

• Synthesis of Polyhydroxylated Quinolizidine and Indolizidine Scaffolds from Sugar-Derived Lactams via a One-Pot Reduction/Mannich/Michael Sequence
  作者：Piotr Szcześniak、Sebastian Stecko、Elżbieta Maziarz、Olga Staszewska-Krajewska、Bartłomiej Furman

  DOI：10.1021/jo502146z

  日期：2014.11.7

  A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz’s reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky’s diene. The stereochemical course of the investigated reaction has been explained in detail

  描述了一种直接合成亚氨基糖的吲哚并立定和喹喔嗪骨架的方法。提出的策略是基于先用Schwartz试剂还原一锅糖内酰胺，然后再将得到的糖亚胺与Danishefsky的二烯进行非对映选择性的Mannich / Michael串联反应。已详细解释了所研究反应的立体化学过程。所获得的双环产物是用于合成各种天然存在的多羟基化生物碱及其衍生物的有吸引力的结构单元。
• Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams
  作者：Michał Mateusz Więcław、Bartłomiej Furman

  DOI：10.3762/bjoc.17.12

  日期：——

  Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a Schwartz’s reagent-mediated reductive amide functionalization followed by a variant of the Ugi–azide multicomponent reaction. The anomeric configurations of two products were unambiguously confirmed by X-ray analysis. This work also describes examples of interesting

  在这里，我们介绍了通过Schwartz试剂介导的还原性酰胺功能化，然后是Ugi-叠氮化物多组分反应的一种变体，从简单的糖中直接直接不对称合成四唑官能化的1-deoxynojirimycin衍生物。通过X射线分析清楚地证实了两种产物的端基异构体构型。这项工作还描述了一些有趣的标题产品转换示例。最后，就其形成机理做了一些令人惊讶的观察。
• Solvent-controlled synthesis of bulky and polar-bulky galactonoamidines
  作者：Susanne Striegler、Ifedi Orizu

  DOI：10.1016/j.carres.2022.108520

  日期：2022.3

  The goal of this study was the design and synthesis of bulky and polar-bulky galactonoamidines that have a potential to interact with both catalytic amino acids in the active site of human α-galactosidase. While a library of more than 25 compounds was previously synthesized following established protocols, the coupling of the selected amines with activated perbenzylated galactothionolactam yielded

  本研究的目的是设计和合成大块和极性大的半乳糖脒，它们有可能与人 α-半乳糖苷酶活性位点中的两种催化氨基酸相互作用。虽然先前按照既定方案合成了超过 25 种化合物的库，但所选胺与活化的过苄基化半乳糖硫内酰胺的偶联对于一些过苄基化目标仅产生少量。一种计算方法揭示了选定加合物的相对能量差异，并建议改变溶剂，然后成功合成 20-75% 的前体化合物。随后尝试通过 Pd 催化氢化对过苄基化半乳糖脒进行全局脱保护，导致不需要的 Pd 配位、不完全脱苄基化反应、部分化合物水解、甚至完全分解。在修改去苄基化条件后，制定了一个冗长的协议来纯化目标碳水化合物衍生物。
• A concise enantioselective synthesis of iminosugar derivatives
  作者：Wei-Wei Liao、Ismail Ibrahem、Armando Córdova

  DOI：10.1039/b516352h

  日期：——

  The concise de novo synthesis of amino- and iminosugar derivatives is presented; the four stereocenters of the iminosugar derivatives are created in two-steps with high chemoselectivity and excellent enantioselectivity.

  介绍了氨基糖和亚氨基糖衍生物的简明从头合成方法；亚氨基糖衍生物的四个立体中心通过两个步骤生成，具有很高的化学选择性和出色的对映选择性。
• An Advantageous Synthesis of 5,6,7,8-Tetra-Hydrotetrazolo[1,5-a]Pyridines
  作者：Stefan Vonhoff、Andrea Vasella

  DOI：10.1080/00397919908085802

  日期：1999.2

  Abstract The one-step synthesis of various O -benzyl-protected glyconotetrazoles from the corresponding glyconolactams is reported. The method is superior to the previously employed cycloaddition of azidonitriles as it uses readily available starting materials and leads to higher yields.

  摘要 报道了从相应的甘醇内酰胺一步法合成各种 O-苄基保护的糖基诺四唑。该方法优于以前使用的叠氮腈环加成，因为它使用容易获得的起始材料并导致更高的产率。