1,2,4,6-tetra-O-acetate-2-O-methyl-α-D-glucopyranoside | 4163-58-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,4,6-tetra-O-acetate-2-O-methyl-α-D-glucopyranoside
• 英文别名: 1,2,4,6-tetra-O-acetyl-3-O-methyl-α-D-glucopyranose；3-O-Methyl-α-D-glucopyranose-tetraacetat；[(2R,3R,4S,5R,6R)-3,5,6-triacetyloxy-4-methoxyoxan-2-yl]methyl acetate
• CAS: 4163-58-0
• 化学式: C₁₅H₂₂O₁₀
• 分子量: 362.334
• InChiKey: DCJXMAVPDMWIOR-QMIVOQANSA-N

物化性质

• 沸点：
  424.3±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,4,6-tetra-O-acetate-2-O-methyl-α-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 生成 2,2-Dimethyl-propionic acid (4aS,6R,7R,8R,8aR)-7-acetoxy-4-amino-8-methoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl ester
  参考文献：
  名称：

  Synthesis and biological activity of artificial analogs of mycalamide A

  摘要：

  Artificial analogs of mycalamide A, a potent antitumor and antiviral compound isolated from a New Zealand marine sponge, were synthesized and their biological activities were tested. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00365-x
• 作为产物：
  描述：

  methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、506.62 kPa 条件下， 反应 36.0h， 生成 1,2,4,6-tetra-O-acetate-2-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084

文献信息

• Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis
  作者：Alexander S. Henderson、John F. Bower、M. Carmen Galan

  DOI：10.1039/c4ob02056a

  日期：——

  Versatile syntheses of C2-linked and C2-symmetric carbohydrate-based imidazol(in)ium salts from functionalised amino-carbohydrate derivatives are reported. The novel NHCs were ligated to [Rh(COD)Cl]2 and evaluated in Rh-catalysed asymmetric hydrosilylation of ketones with good yields and promising enantioselectivities.

  报道了从官能化的氨基碳水化合物衍生物多功能合成C 2连接的和C 2对称的基于碳水化合物的咪唑盐。将新型NHC连接到[Rh（COD）Cl] 2上，并在Rh催化的酮的不对称氢化硅烷化中进行了评估，产率高，对映选择性高。
• Lipophilic sugar nucleotide synthesis by structure-based design of nucleotidylyltransferase substrates
  作者：Malcolm P. Huestis、Gaia A. Aish、Joseph P. M. Hui、Evelyn C. Soo、David L. Jakeman

  DOI：10.1039/b716955h

  日期：——

  Structure-based design of alkyl sugar-1-phosphates provides an efficient nucleotidylyltransferase-catalyzed synthesis of a series of new lipophilic sugar nucleotides possessing long or branched alkyl chains, thereby demonstrating the utility of nucleotidylyltransferases to catalyze the synthesis of sugar nucleotides with potential applications in lipopolysaccharide and lipoglycopeptide biosynthesis.

  基于结构的烷基糖-1-磷酸酯设计提供了一种高效的核苷酸转移酶催化合成一系列新型脂溶性糖核苷酸的方法，这些糖核苷酸具有较长或支链的烷基链，从而展示了核苷酸转移酶在催化合成具有潜在应用于脂多糖和脂糖肽生物合成的糖核苷酸方面的实用性。
• POLYSACCHARIDES SYNTHETIQUES, PROCEDE POUR LEUR PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SANOFI-SYNTHELABO

  公开号：EP0912613B1

  公开（公告）日：2002-09-25
• US6534481B1
  申请人：——

  公开号：US6534481B1

  公开（公告）日：2003-03-18