benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside | 61134-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: Benzyl-3,4,6-tri-O-benzyl-α-D-mannopyranosid；benzyl 3,4,6-tri-O-benzyl-α-mannopyranoside；1,3,4,6-tetra-O-benzyl-α-D-mannopyranoside；benzyl 3,4,6-tri-O-benzyl-α-D-mannoside；benzyl 3,4,6-tri-O-benzyl-alpha-D-mannopyranoside；(2S,3S,4R,5R,6R)-2,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 61134-30-3
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: AFHZEIVSXDXEMO-OHBKMZHCSA-N

物化性质

• 沸点：
  676.1±55.0 °C(Predicted)
• 密度：
  1.22±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：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 N-Benzyl-2-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-N-{[2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethylcarbamoyl]-methyl}-acetamide
  参考文献：
  名称：

  Application of the four-component Ugi condensation for the preparation of sulfated glycoconjugate libraries

  摘要：

  A focused library of novel, sulfated glycoconjugates was synthesized by utilizing carbohydrate-derived blocks in the four-component Ugi condensation. Library members comprise a sulfated monosaccharide linked by various spacers to either in aromatic or monosulfated moiety, or a second sulfated monosaccharide. The affinities of these heparan sulfate (HS) mimetics for the HS-binding fibroblast growth factors FGF-1 and FGF-2 were measured via a surface plasmon resonance solution affinity assay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.017
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 sodium methylate sodium methylate 、 sodium hydride 、 mercury dibromide 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 29.0h， 生成 benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of linear d-mannotetraose and d-mannohexaose, partial structures of the cell-surface d-mannan of Candida albicans and Candida utilis

  摘要：

  DOI：

  10.1016/s0008-6215(00)82588-4

文献信息

• Bimodal Glycosyl Donors Protected by 2-<i>O-</i>(<i>ortho</i>-Tosylamido)benzyl Group
  作者：Feiqing Ding、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1021/acs.orglett.8b01922

  日期：2018.7.20

  A glucosyl donor equipped with C2-o-TsNHbenzyl ether was shown to provide both α- and β-glycosides stereoselectivity, by changing the reaction conditions. Namely, β-glycosides were selectively obtained when the trichloroacetimidate was activated by Tf2NH. On the other hand, activation by TfOH in Et2O provided α-glycosides as major products. This “single donor” approach was employed to assemble naturally

  通过改变反应条件，显示了配备有C 2 -o- TsNH苄基醚的葡糖基供体同时提供α-和β-糖苷的立体选择性。即，当通过Tf 2 NH激活三氯乙酰亚胺酸酯时，选择性地获得β-糖苷。另一方面，通过TfOH在Et 2 O中的活化提供了α-糖苷作为主要产物。这种“单一供体”的方法被用来装配自然三糖α-发生d -Glc-（→2 1）-α- d -Glc-（1→6） - d -Glc和它的端基异构体。
• The rapid synthesis of deoxyfluoro sugars using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)
  作者：Bogdan Doboszewski、George W. Hay、Walter A. Szarek

  DOI：10.1139/v87-070

  日期：1987.2.1

  Deoxyfluoro sugars were synthesized rapidly by the reaction of trifluoromethanesulfonyl derivatives of partially protected sugars with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) under mild conditions. The displacements occurred with inversion of configuration; fluorine has been introduced stereospecifically at each of the secondary alcoholic sites of aldohexopyranosides and in one

  脱氧氟糖是通过部分保护糖的三氟甲磺酰基衍生物与三（二甲氨基）锍二氟三甲基硅酸盐（TASF）在温和条件下反应快速合成的。位移发生于构型反转；在吡喃醛糖苷的每个二级醇位点和呋喃类系统的一个例子中，氟已被立体定向​​地引入。在某些情况下，会产生不含氟的不饱和化合物。
• ZnI₂-Directed Stereocontrolled α-Glucosylation
  作者：Siai Zhou、Xuemei Zhong、Aoxin Guo、Qian Xiao、Jiaming Ao、Wanmeng Zhu、Hui Cai、Akihiro Ishiwata、Yukishige Ito、Xue-Wei Liu、Feiqing Ding

  DOI：10.1021/acs.orglett.1c02405

  日期：2021.9.3

  Here we report a glucosylation strategy mediated by ZnI2, a cheap and mild Lewis acid, for the highly stereoselective construction of 1,2-cis-O-glycosidic linkages using easily accessible and common 4,6-O-tethered glucosyl donors. The versatility and effectiveness of the α-glucosylation strategy were demonstrated successfully with various acceptors, including complex alcohols. This approach demonstrates

  在这里，我们报告了一种由廉价和温和的路易斯酸 ZnI 2介导的糖基化策略，用于使用易于获得和常见的 4,6 - O-束缚葡萄糖基供体高度立体选择性地构建 1,2-顺式-O-糖苷键。α-葡糖基化策略的多功能性和有效性已通过各种受体（包括复合醇）成功证明。这种方法证明了模块化合成具有线性和支链骨架结构的各种 α-葡聚糖的可行性。
• Comparing n-pentenyl orthoesters and n-pentenyl glycosides as alternative glycosyl donors
  作者：Mateusz Mach、Urs Schlueter、Felix Mathew、Bert Fraser-Reid、Kevin C Hazen

  DOI：10.1016/s0040-4020(02)00671-3

  日期：2002.9

  As is well known, cyclic 1,2-glycosyl orthoesters undergo ready acid catalyzed rearrangement to 2-O-acyl glycosides in which the alkoxy group is transferred from the orthoester to the anomeric center in a highly stereocontrolled process. The related n-pentenyl derivatives are unique in that either the orthoester (NPOE) or its rearrangement product (NPGAC) can function as a glycosyl donor, and mechanistic

  众所周知，环状1，2-糖基原酸酯经历了容易的酸催化重排成2- O-酰基糖苷，其中烷氧基以高度立体可控的过程从原酸酯转移到异头中心。相关的正戊烯基衍生物的独特之处在于原酸酯（NPOE）或它的重排产物（NPG AC）都可以作为糖基供体，并且从机械方面的考虑来看，两者都应该（或可能！）产生相同的产物。 ）是由反式原酸酯化，糖苷化，糖基酯化等产生的。实验表明，通过精心选择供体，NPOE或相关的NPG AC，可以优化从给定反应获得的产物，并特别注意反应条件，亲电子启动子，糖基受体的“大小”和实验方案。
• The synthesis of phosphorylated disaccharide components of the extracellular phosphomannan of Pichia (Hansenula) holstii NRRL Y-2448
  作者：Jon K. Fairweather、Tomislav Karoli、Vito Ferro

  DOI：10.1016/j.bmc.2004.09.005

  日期：2004.12

  Methods for the stereoselective synthesis of alpha-(1-->2)- and alpha-(1-->3)-linked 6(II)-O-phosphomannobiosides were developed. Two strategies were successfully employed: a D-mannosyl acceptor was coupled with a phosphorylated D-mannosyl trichloroacetimidate donor, or alternatively with a differentially 6-O-protected D-mannosyl trichloroacetimidate donor which, after glycosylation, was selectively

  开发了立体选择性合成α-（1-> 2）-和α-（1-> 3）连接的6（II）-O-磷酸甘露糖苷的方法。成功地采用了两种策略：将D-甘露糖基受体与磷酸化的D-甘露糖基三氯乙酰亚氨酸酯供体偶联，或者与差异化的6-O-保护的D-甘露糖基三氯乙酰亚氨酸酯供体偶联，其在糖基化之后被选择性地脱保护并磷酸化。打算用于抗血管生成药物候选物PI-88、2-O-（6-O-磷酸-α-D-甘露吡喃糖基）-D-甘露吡喃糖和甲基3-O-（6-O-合成了磷酸-α-D-甘露吡喃糖基）-α-D-甘露吡喃糖苷。前者是毕赤酵母NRRL Y-2448胞外磷酸甘露聚糖侧链重复单元的次要成分，