methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside | 73111-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 73111-53-2
• 化学式: C₂₈H₃₂O₆
• 分子量: 464.558
• InChiKey: MOKYEUQDXDKNDX-URYJJRPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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 2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-2-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Studies on the synthesis of two tetrasaccharides and the reactivity difference between them

  摘要：

  Studies on the reactivity of two synthetic tetrasaccharides as glycosyl accepters showed that condensation of the methyl alpha-glycoside with a disaccharide donor afforded a hexasaccharide, but condensation of the methyl beta-glycoside with the disaccharide did not yield the corresponding hexasaccharide under the same conditions. A combination of theoretical results and 2D NMR indicated that the reactivity difference between the methyl alpha-glycoside and the methyl beta-glycoside was determined mainly by steric effects. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00169-9
• 作为产物：
  描述：

  C₃₀H₃₄O₇ 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以99%的产率得到methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of an antimetastatic tetrasaccharide β-d-Gal-(1→4)-β-d-GlcpNAc-(1→6)-α-d-Manp-(1→6)-β-d-Manp-OMe

  摘要：

  An antimetastatic tetrasaccharide T-1, beta-D-Gal-(1 -> 4)-beta-D-GlcpNAc-(1 -> 6)-alpha-D-Manp-(1 -> 6)-beta-D-Manp-OMe, was synthesized with two approaches. The first approach was a conventional method employing thioglycoside and Koenigs-Knorr glycosylation reaction in 24% overall yield. The second one was a novel route through the azidoiodo-glycosylation strategy by using 2-iodo-2-deoxylactosyl azide as the donor in 36% overall yield. (C) 2012 Zhong Jun Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.10.022

文献信息

• Constrained 3,6-Anhydro-Heptosides: Synthesis by a DAST-Induced Debenzylative Reaction, and Reactivity Profile
  作者：Abdellatif Tikad、Stéphane P. Vincent

  DOI：10.1002/ejoc.201301071

  日期：2013.11

  We report the first synthesis of a conformationally constrained 3,6-anhydroheptoside analogue of D-glycero-Dmanno-heptopyranose 7-phosphate by a DAST (diethylaminosulfur trifluoride)-induced intramolecular cycloetherification. The reactivity of a series of constrained bicyclic 3,6anhydro-thioheptosides as glycosyl donors was also studied

  我们报告了通过 DAST（二乙氨基三氟化硫）诱导的分子内环醚化首次合成 D-甘油-D-甘露糖-吡喃庚糖 7-磷酸的构象受限的 3,6-脱水庚糖苷类似物。还研究了一系列受约束的双环 3,6anhydro-thioheptosides 作为糖基供体的反应性
• WO2006/91790
  申请人：——

  公开号：——

  公开（公告）日：——
• Schmidt, Richard R.; Moering, Ute; Reichrath, Manfred, Chemische Berichte, 1982, vol. 115, # 1, p. 39 - 49
  作者：Schmidt, Richard R.、Moering, Ute、Reichrath, Manfred

  DOI：——

  日期：——
• Studies on the synthesis of two tetrasaccharides and the reactivity difference between them
  作者：Xiao-Xiang Zhu、Meng-Shen Cai、Rou-Li Zhou

  DOI：10.1016/s0008-6215(97)00169-9

  日期：1997.9

  Studies on the reactivity of two synthetic tetrasaccharides as glycosyl accepters showed that condensation of the methyl alpha-glycoside with a disaccharide donor afforded a hexasaccharide, but condensation of the methyl beta-glycoside with the disaccharide did not yield the corresponding hexasaccharide under the same conditions. A combination of theoretical results and 2D NMR indicated that the reactivity difference between the methyl alpha-glycoside and the methyl beta-glycoside was determined mainly by steric effects. (C) 1997 Elsevier Science Ltd.
• Synthesis of an antimetastatic tetrasaccharide β-d-Gal-(1→4)-β-d-GlcpNAc-(1→6)-α-d-Manp-(1→6)-β-d-Manp-OMe
  作者：Kai Jun Liao、Xiao Feng Jin、Xiang Bao Meng、Chen Li、Zhong Jun Li

  DOI：10.1016/j.cclet.2012.10.022

  日期：2012.12

  An antimetastatic tetrasaccharide T-1, beta-D-Gal-(1 -> 4)-beta-D-GlcpNAc-(1 -> 6)-alpha-D-Manp-(1 -> 6)-beta-D-Manp-OMe, was synthesized with two approaches. The first approach was a conventional method employing thioglycoside and Koenigs-Knorr glycosylation reaction in 24% overall yield. The second one was a novel route through the azidoiodo-glycosylation strategy by using 2-iodo-2-deoxylactosyl azide as the donor in 36% overall yield. (C) 2012 Zhong Jun Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.