methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside | 6748-94-3

• 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-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• 英文别名: methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-acetylamino-α-D-glucopyranose；methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-N-acetyl-α-D-glucopyranose；methyl-[O³-acetyl-2-acetylamino-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-α-D-glucopyranoside]；Methyl-[O³-acetyl-2-acetylamino-O⁴,O⁶-((Ξ)-benzyliden)-2-desoxy-α-D-glucopyranosid]；Methyl-2-acetamido-3-O-acetyl-4,6-O-benzyliden-2-desoxy-α-D-glucopyranosid；Methyl-2-acetamino-3-O-acetyl-4,6-O-benzyliden-2-desoxy-α-D-glucopyranosid；Methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside；[(4aR,6S,7R,8R,8aS)-7-acetamido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS: 6748-94-3
• 化学式: C₁₈H₂₃NO₇
• 分子量: 365.383
• InChiKey: YPGVKYJNVZUEKA-LPETVPRMSA-N

物化性质

• 熔点：
  235 °C
• 沸点：
  550.9±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 氢氧化钾 、 Amberlite IRA 400 (OH^--form) 、 碘 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 Methyl 2-acetamido-2-deoxy-3-O-(p-methoxybenzyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of ligands related to the O-specific antigen of type 1 Shigella dysenteriae. 3. Glycosylation of 4,6-O-substituted derivatives of methyl 2-acetamido-2-deoxy-.alpha.-D-glucopyranoside with glycosyl donors derived from mono- and oligosaccharides.

  摘要：

  Methyl O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside, obtained by silver trifluoromethanesulfonate-mediated condensation of methyl 2,4-di-O-benzoyl-alpha-L-rhamnopyranoside and 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl bromide (3), was cleaved with dichloromethyl methyl ether (DCMME) to give O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl chloride (9). Condensations of 1,3,4,6-tetra-O-acetyl-alpha-D-galactopyranose with 3 and 9, followed by treatment of the products with DCMME yielded, respectively, glycosyl chlorides 12 and 17. Each of these, as well as 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride was condensed with 4,6-O-substituted (benzylidene, tetraisopropyl-disiloxane-1,3-diyl, or benzyl) derivatives of methyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside, using CH2Cl2, ether, or a mixture thereof as the solvent. The formation of the desired alpha-D-galactopyranosyl linkage was favored when ether was the solvent. Under these conditions, however, the combined yield of the condensation products decreased, especially when less reactive synthons were used. The alpha-linked products obtained were deprotected to give the methyl alpha-glycosides of the tetra, tri-, and the disaccharide related to the chemical repeating unit of the O-specific side chain of the lipopolysaccharide of Shigella dysenteriae type 1. Synthesis of methyl alpha-glycosides of three other constituents of the same polymeric antigen [alpha-L-Rha-(1 --> 3)-alpha-L-Rha, alpha-L-Rha-(1 --> 2)-alpha-D-Gal, and alpha-L-Rha-(1 --> 3)-alpha-L-Rha-(1 --> 2)-alpha-D-Gal] are also described.

  DOI：

  10.1021/jo00034a047
• 作为产物：
  描述：

  methyl N-acetyl-D-glucosamine 在 吡啶 、 zinc(II) chloride 作用下， 反应 48.0h， 生成 methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Preparative routes to methyl 2-acetamido-2,6-dideoxy-α-d-glucopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(83)84058-0

文献信息

• General and Chemoselective N-Transacylation of Secondary Amides by Means of Perfluorinated Anhydrides
  作者：Paola Rota、Pietro Allevi、Raffaele Colombo、Maria L. Costa、Mario Anastasia

  DOI：10.1002/anie.200906055

  日期：2010.3.1

  A direct route: The N‐transacylation of secondary amides to their perfluorinated analogues with the possibility of subsequent conversion into a normal amide is reported (see scheme). This reaction occurs in the presence of a variety of functional groups that are labile to the hydrolysis conditions required by classical N‐transacylation.

  直接途径：报道了仲酰胺经N-酰化成全氟化类似物的可能性，随后可能转化为正酰胺（见方案）。该反应在多种官能团的存在下发生，这些官能团对经典的N-酰化反应所需的水解条件不利。
• High yielding N-transacylation of secondary amides in acids labile molecules by the action of perfluorinated anhydrides in the presence of a mild base
  作者：Paola Rota、Pietro Allevi、Maria L. Costa、Mario Anastasia

  DOI：10.1016/j.tetasy.2010.10.019

  日期：2010.11

  The simple addition of mild bases (Et3N or DIPEA) allows a high yielding N-transacylation of secondary amides, performed by perfluorinated anhydrides, in molecules that are very sensitive to acids.

  简单添加温和的碱（Et 3 N或DIPEA）可以在对酸非常敏感的分子中通过全氟化酸酐进行仲酰胺的高收率N-酰基转移。
• 4. Some observations on the ring scission of 4 : 6-benzylidene 2 : 3-anhydro α-methylmannoside with ammonia
  作者：L. F. Wiggins

  DOI：10.1039/jr9470000018

  日期：——
• Meyer zu Reckendorf; Bonner, Chemische Berichte, 1961, vol. 94, p. 3293,3296
  作者：Meyer zu Reckendorf、Bonner

  DOI：——

  日期：——
• TSUDA, YOSHISUKE;OKUNO, YUKIHIRO;IWAKI, MINORU;KANEMITSU, KIMIHIRO, CHEM. AND PHARM. BULL., 37,(1989) N0, C. 2673-2678
  作者：TSUDA, YOSHISUKE、OKUNO, YUKIHIRO、IWAKI, MINORU、KANEMITSU, KIMIHIRO

  DOI：——

  日期：——