methyl 3,4,6-tri-O-acetyl-α-D-mannopyranoside | 20771-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4R,5S,6S)-3,4-diacetyloxy-5-hydroxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 20771-15-7；51295-60-4；51295-71-7；51295-72-8；117677-28-8；131233-87-9
• 化学式: C₁₃H₂₀O₉
• 分子量: 320.296
• InChiKey: DBGZTJNHXHDWAP-MLGHIDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 4,6-di-O-acetyl-α-D-mannopyranoside 在 吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3,4,6-tri-O-acetyl-α-D-mannopyranoside 、 methyl 2,4,6-tri-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Regioselective glycosylation reactions based on computational predictions

  摘要：

  Regioselectivity is a major issue in glycosylation reactions. Better understanding of regioselectivity of acceptors can greatly facilitate and simplify the syntheses of oligosaccharides. The reactivity of diol acceptors is often affected by stereochemistry and protecting groups, which make prediction the regioselectivity of diol acceptors extremely difficult. Quantum mechanic methods were used to study the relationship between protecting groups and reactivity of diol acceptor and a correlation between Fukui function and regioselectivity is established through series of glycosylation reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.044

文献信息

• Methyl 1,2-Orthoesters as Useful Glycosyl Donors in Glycosylation Reactions: A Comparison with n-Pent-4-enyl 1,2-Orthoesters
  作者：Clara Uriel、Juan Ventura、Ana M. Gómez、J. Cristóbal López、Bert Fraser-Reid

  DOI：10.1002/ejoc.201200089

  日期：2012.6

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors – upon BF3·Et2O activation in CH2Cl2 – in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective

  吡喃甘露糖衍生的 1,2- 原乙酸甲酯 (R = Me) 和 -苯甲酸酯 (R = Ph) 可以作为糖基供体 - 在 CH2Cl2 中 BF3·Et2O 活化后 - 在与单糖受体的糖基化反应中以良好的收率提供二糖。在该过程中，糖基化优于酸催化重排，导致甲基吡喃甘露糖苷。甲基 1,2-原酸酯也可用于单糖二醇的区域选择性糖基化方案，其中它们显示出良好的区域选择性。
• Novel methods for the preparation of partially acetylated carbohydrates
  作者：Stephen Hanessian、Masahiro Kagotani

  DOI：10.1016/0008-6215(90)84071-2

  日期：1990.7

  Abstract The selective acetylation of methyl a - d -hexopyranosides in the presence of zinc chloride shows unusual reactivity patterns compared to control experiments. Hydroperoxide ion is a mild and selective deacetylation reagent which does not attack primary acetates.

  摘要在氯化锌存在下，甲基α-d-己吡喃糖苷的选择性乙酰化与对照实验相比，显示出不同寻常的反应模式。氢过氧化物离子是一种温和的，选择性的脱乙酰基试剂，不会侵蚀初级乙酸盐。
• Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO
  作者：Pavel Cheshev、Alberto Marra、Alessandro Dondoni

  DOI：10.1016/j.carres.2006.09.003

  日期：2006.11

  A multi-gram epoxidation of 3,4,6-tri-O-benzyl-D-glucal and D-galactal with dimethyldioxirane (DMDO) generated in situ from Oxone (R)/acetone in a biphasic system (CH2Cl2-aqueous NaHCO3) resulted in the formation of the corresponding 1,2-anhydrosugars in a 99% yield and 100% selectivity. In a similar way, 3,4,6-tri-O-acetyl-D-glucal afforded a 7:1 mixture of the corresponding gluco and manno derivatives in an 87% overall yield. (c) 2006 Elsevier Ltd. All rights reserved.
• HANESSIAN, STEPHEN;KAGOTANI, MASAHIRO, CARBOHYDR. RES., 202,(1990) C. 67-79
  作者：HANESSIAN, STEPHEN、KAGOTANI, MASAHIRO

  DOI：——

  日期：——