(3aR,4S,6R,7S,7aR)-7-hydroxy-4-(4-methoxyphenoxy)-6-(phenylmethoxymethyl)-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-2-one | 1340541-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,6R,7S,7aR)-7-hydroxy-4-(4-methoxyphenoxy)-6-(phenylmethoxymethyl)-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-2-one
• CAS: 1340541-48-1
• 化学式: C₂₁H₂₃NO₇
• 分子量: 401.416
• InChiKey: PZTFYNOMUXRSSR-LASHMREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,4S,6R,7S,7aR)-7-hydroxy-4-(4-methoxyphenoxy)-6-(phenylmethoxymethyl)-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-2-one 、 以 二氯甲烷 为溶剂， 反应 1.5h， 以90 mg的产率得到p-methoxyphenyl 2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-4-O-(methyl 3-Obenzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)-β-D-glucopyranoside
  参考文献：
  名称：

  Strict Stereocontrol by 2,4-O-Di-tert-butylsilylene Group on β-Glucuronylations

  摘要：

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.

  DOI：

  10.1021/ol300634x
• 作为产物：
  描述：

  4-methoxyphenyl 2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-β-D-glucopyranoside 在 三乙基硅烷 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 (3aR,4S,6R,7S,7aR)-7-hydroxy-4-(4-methoxyphenoxy)-6-(phenylmethoxymethyl)-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-2-one
  参考文献：
  名称：

  Substituent effects in endocyclic cleavage–recyclization anomerization reaction of pyranosides

  摘要：

  Pyranosides with 2,3-trans carbamate or 2,3-trans carbonate groups are anomerized under mild acidic conditions via endocyclic cleavage reaction. In order to understand the nature of the anomerization reaction via the endocyclic cleavage recyclization process, the substituent effects at various positions were investigated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.059

文献信息

• Significant Substituent Effect on the Anomerization of Pyranosides: Mechanism of Anomerization and Synthesis of a 1,2-<i>cis</i>Glucosamine Oligomer from the 1,2-<i>trans</i>Anomer
  作者：Shino Manabe、Hiroko Satoh、Jürg Hutter、Hans Peter Lüthi、Teodoro Laino、Yukishige Ito

  DOI：10.1002/chem.201303474

  日期：2014.1.3

  Aminoglycosides containing a 2,3‐trans carbamate group easily undergo anomerization from the 1,2‐trans glycoside to the 1,2‐cis isomer under mild acidic conditions. The N‐substituent of the carbamate has a significant effect on the anomerization reaction; in particular, an N‐acetyl group facilitated rapid and complete α‐anomerization. The differences in reactivity due to the various N‐substituents were

  在弱酸性条件下，含有2,3-反式氨基甲酸酯基团的氨基糖苷很容易从1,2-反式糖苷变为1,2-顺式异构体。氨基甲酸酯的N-取代基对异构化反应有显着影响。特别是，N-乙酰基促进了快速和完全的α-异构化。DFT计算的结果支持了由于各种N取代基引起的反应性差异。发现乙酰基羰基的接近异头位置的方向显着地促进了异构化反应的进行。通过利用该反应，可形成具有多个1,2-顺式的低聚氨基糖苷糖苷键是通过一个步骤从1,2-反式糖苷生成的。
• Substituent effects in endocyclic cleavage–recyclization anomerization reaction of pyranosides
  作者：Shino Manabe、Kazuyuki Ishii、Hiroko Satoh、Yukishige Ito

  DOI：10.1016/j.tet.2011.09.059

  日期：2011.12

  Pyranosides with 2,3-trans carbamate or 2,3-trans carbonate groups are anomerized under mild acidic conditions via endocyclic cleavage reaction. In order to understand the nature of the anomerization reaction via the endocyclic cleavage recyclization process, the substituent effects at various positions were investigated. (C) 2011 Elsevier Ltd. All rights reserved.
• Strict Stereocontrol by 2,4-<i>O</i>-Di-<i>tert</i>-butylsilylene Group on β-Glucuronylations
  作者：Takayuki Furukawa、Hiroshi Hinou、Shin-Ichiro Nishimura

  DOI：10.1021/ol300634x

  日期：2012.4.20

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.