methyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside | 23392-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• 英文别名: (4aR,6S,7S,8S,8aS)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 23392-29-2
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: FYUXMZUFURHCOX-MQCITOEMSA-N

物化性质

• 沸点：
  541.1±50.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  methyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 在 molecular sieve 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 Methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of methyl 3-O-a-d-galactopyranosyl-6-O-a-d-mannopyranosyl-a-d-mannopyranoside, methyl 3-O-a-d-glucopyranosyl-6-O-a-d-mannopyranosyl-a-d-mannopyranoside, methyl 6-O-a-d-galactopyranosyl-3-O-a-d-mannopyranosyl-a-d-mannopyranoside, and methyl 6-O-a-d-glucopyranosyl-3-O-a-d-mannopyranosyl-a-d-mannopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(90)84213-e
• 作为产物：
  描述：

  (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 、 溴甲苯 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以16%的产率得到methyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Partial benzylation of methyl 4,6-O-benzylidene-α-d-mannopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(83)88391-8

文献信息

• Allyl protecting group mediated intramolecular aglycon delivery (IAD): synthesis of α-glucofuranosides and β-rhamnopyranosides
  作者：Ian Cumpstey、Antony J. Fairbanks、Alison J. Redgrave

  DOI：10.1016/j.tet.2004.07.083

  日期：2004.10

  The use of allyl protecting group mediated intramolecular aglycon delivery (IAD) as a strategy for intramolecular glycosylation has been extended to allow the stereoselective synthesis of α-glucofuranosides and β-rhamnopyranosides, in a totally stereoselective fashion. The efficiency of intramolecular glycosylation is dependent on the protecting group pattern of the glycosyl donor, and on the steric

  使用烯丙基保护基介导的分子内糖苷配基（IAD）作为分子内糖基化的策略已得到扩展，以完全立体选择性的方式允许α-葡糖呋喃糖苷和β-鼠李糖吡喃糖苷的立体选择性合成。分子内糖基化的效率取决于糖基供体的保护基团模式以及糖基受体的空间体积。
• One pot conversion of carbohydrates alcohol into chloride via benzotriazole sulfonate
  作者：Chandra S. Azad、Anil K. Saxena

  DOI：10.1016/j.tet.2013.01.044

  日期：2013.3

  A one pot method for chloro-dehydroxylation of carbohydrates alcohol including sterically and electrically hindered ones in excellent yield was developed. The benzotriazole-1-sulfonate proposed to play a crucial role in the reaction medium, which undergoes substitution by chloride ion in the reaction medium to give only desired chloride derivative without the formation of side product. The optimized

  开发了一种单罐方法，用于碳水化合物醇的氯脱羟基反应，包括空间位阻和电位受阻的醇，均具有优异的收率。提出苯并三唑-1-磺酸盐在反应介质中起关键作用，该反应介质在反应介质中被氯离子取代，仅得到所需的氯衍生物，而没有副产物的形成。优化的方法可用于多种生物活性化合物或手性合成酮的合成。
• Use of a phenyl 1-selenogalactofuranoside as a glycosyl donor for the synthesis of galactofuranosyl-containing disaccharides
  作者：Blair D. Johnston、B.Mario Pinto

  DOI：10.1016/s0008-6215(97)10016-7

  日期：1997.12

  The use of acetylated phenyl 1-seleno-beta-D-galactofuranoside as a glycosyl donor for the synthesis of protected D-Galf-beta-(1-->3)-alpha-D-Manp as its methyl or ethylthio glycoside has been demonstrated. Activation of the selenoglycoside over a thioglycoside acceptor by NIS/TfOH is extremely selective and gives the ethylthio disaccharide in 91% yield. The parent disaccharide is found as a terminal

  已使用乙酰化的苯基1-硒基-β-D-半乳糖呋喃糖苷作为糖基供体，用于合成受保护的D-Galf-β-（1-> 3）-α-D-Manp，作为其甲基或乙硫基糖苷。演示。NIS / TfOH在硫代糖苷受体上激活硒代糖苷具有极高的选择性，并以91％的收率得到乙硫基二糖。亲本二糖被发现为原生动物锥虫锥虫锥虫的脂肽基磷酸聚糖寡糖的末端和分支单元，锥虫是南美锥虫病的致病因子。
• Synthesis, NMR, and conformational studies of methyl α-d-mannopyranoside 2-, 3-, 4-, and 6-monophosphates
  作者：Christian Bernlind、Stefan Oscarson、Göran Widmalm

  DOI：10.1016/0008-6215(94)00169-3

  日期：1994.10

  syntheses of methyl α- d -mannopyranoside 2-, 3-4-, and 6-phosphate disodium salts are described. 1H, 13C, and 31P NMR spectra of the four monophosphates were recorded, fully assigned, and compared to nonphosphorylated methyl α- d -mannopyranoside in order to obtain chemical shift changes due to phosphorylation. The magnitude of these changes are up to 0.45 ppm for 1H and 3.0 ppm for 13C NMR spectra. The

  摘要描述了甲基α-d-甘露吡喃糖苷2-，3-4-和6-磷酸二钠盐的合成。记录，完全分配了这四种单磷酸的1H，13C和31P NMR光谱，并将其与未磷酸化的甲基α-d-甘露吡喃糖苷进行比较，以获得由于磷酸化引起的化学位移变化。这些变化的幅度对于1H高达0.45 ppm，对于13C NMR谱高达3.0 ppm。还计算了四种化合物中磷酸基团的优选取向。
• SACCHARIDE CONJUGATES
  申请人：ARIZONA BOARD OF REGENTS, for and on behalf of ARIZONA STATE UNIVERSITY

  公开号：US20160038615A1

  公开（公告）日：2016-02-11

  This invention relates to compounds comprising a saccharide conjugated to an imaging agent or a reporter group, compositions comprising them and methods of using them. Specifically BLM-disaccharide and BLM-monosaccharide conjugates containing different linker groups and an imaging agent or a reporter group are provided for the targeting and imaging of tumors.

  本发明涉及包含糖链与成像剂或报告基团偶联的化合物、包含它们的组合物以及使用它们的方法。具体提供了含有不同连接基团和成像剂或报告基团的BLM-双糖和BLM-单糖共轭物，用于靶向和成像肿瘤。