11,14-二氧杂-2,9-二氮杂十七碳-16-烯酸,4,6,6,16-四甲基-10,15-二羰基-,2-[(2-甲基-1-羰基-2-丙烯-1-基)氧代]乙基酯 | 74560-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 中文名称: 11,14-二氧杂-2,9-二氮杂十七碳-16-烯酸,4,6,6,16-四甲基-10,15-二羰基-,2-[(2-甲基-1-羰基-2-丙烯-1-基)氧代]乙基酯
• 英文名称: methyl 4,6-O-benzylidene-α-D-idopyranoside
• 英文别名: methyl 4,6-O-(S)-benzylidene-α-D-idopyranoside；(2S,4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 74560-56-8
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: VVSWDMJYIDBTMV-ORWNZLQRSA-N

物化性质

• 沸点：
  473.0±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  11,14-二氧杂-2,9-二氮杂十七碳-16-烯酸,4,6,6,16-四甲基-10,15-二羰基-,2-[(2-甲基-1-羰基-2-丙烯-1-基)氧代]乙基酯 在 silver(l) oxide 、 碘甲烷 作用下， 生成 3-chloro-5-(4-chlorophenyl)-N-(2-morpholin-4-ium-4-ylethyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide
  参考文献：
  名称：

  α甲基d -idoside- <1,5> -单甲基醚（2），和- （3）

  摘要：

  DOI：

  10.1002/hlca.660280127
• 作为产物：
  描述：

  Methyl 2,3-anhydro-4,6-O-benzylidene-α-D-talopyranoside 在 氢氧化钾 作用下， 生成 11,14-二氧杂-2,9-二氮杂十七碳-16-烯酸,4,6,6,16-四甲基-10,15-二羰基-,2-[(2-甲基-1-羰基-2-丙烯-1-基)氧代]乙基酯
  参考文献：
  名称：

  d-理想a d（+）-半乳糖

  摘要：

  DOI：

  10.1002/hlca.19450280102

文献信息

• Utilization of Sugars in Organic Synthesis; Part XXVII. Chemistry of Oxo-Sugars. (2). Regio- and Stereo-Selective Synthesis of Methyl D-Hexopyranosiduloses and Identification of Their Forms Existing in Solutions.
  作者：Hong-Min LIU、Yoshiyuki SATO、Yoshisuke TSUDA

  DOI：10.1248/cpb.41.491

  日期：——

  Sixteen oxo derivatives of methyl D-hexopyranosides with various regio- and stereo-chemistries were selectively synthesized by direct oxidation of non-protected methyl glycosides by the bistributyltin oxide-bromine method or by oxidation of pfrtially protected glycosides followed by deprotection. The forms of these oxoglycosides existing in pryidine-d5 and in H2O (D2O) were investigated by means of 13C-NMR spectroscopy, and it was found that interconversion between oxo and hydrate forms of oxoglycosides readily takes place.

  通过双二丁基氧化锡-溴法直接氧化未受保护的甲基糖苷，或先氧化受部分保护的糖苷再进行脱保护，选择性地合成了十六种具有不同区域和立体化学结构的甲基 D-吡喃己苷的氧化衍生物。通过 13C-NMR 光谱法研究了这些氧化糖苷在 Pryidine-d5 和 H2O（D2O）中的存在形式，发现氧化糖苷的氧化形式和水合物形式之间很容易发生相互转化。
• A new and versatile method for the preparation of unsaturated sugars
  作者：Michel Bessodes、Elie Abushanab、Raymond P. Panzica

  DOI：10.1039/c39810000026

  日期：——

  Reaction of vicinal diols with iodoform, tri-phenylphosphine, and imidazole gives the corresponding olefin in high to moderate yields.

  邻位二醇与碘仿，三苯基膦和咪唑的反应以高到中等的产率得到相应的烯烃。
• The 4,6-benzylidene acetals, and the conformation, of methyl α-d-idopyranoside
  作者：Stephen J. Angyal、Yôtaro Kondo

  DOI：10.1016/s0008-6215(00)85675-x

  日期：1980.5
• Regioselectivity in the sulfation of dermatan sulfate and methyl 4,6-O-benzylidene-α-d-idopyranoside
  作者：Karla G. Ludwig-Baxter、Zhengchun Liu、Arthur S. Perlin

  DOI：10.1016/0008-6215(91)80032-i

  日期：1991.7

  The sulfation of dermatan sulfate by SO3-trimethylamine in N,N-dimethylformamide led to substitution initially at HO-6 of residues of 2-acetamido-2-deoxy-beta-D-galactopyranosyl4-sulfate (1), to produce the 4,6-disulfate (6). When this step reached a level of > 50%, sulfation occurred with equal facility at HO-2 and HO-3 of residues of alpha-L-idopyranosyluronic acid (2), giving rise to a mixture of 2-, 3-, and 2,3-disulfates. An analogous substitution pattern was observed for HO-2 and -3 of a simpler idopyranose unit, in the sulfation of methyl 4,6-O-benzylidene-alpha-D-idopyranoside (12). This lack of regioselectivity in the reaction of 2 (and 12) constrasts markedly with the high affinity of the reagent for HO-3 of residues of alpha-L-idopyranosyluronic acid present in a modified form of heparin. It is attributed to a difference between the two polymers in the relative orientation of their neighboring amino sugar residues, whereby there is an unobstructed access of the reagent in one instance, and hindrance of HO-2 selectively in the other. Enzymolysis by chondroitinase ABC was found to yield unsaturated disaccharide containing residues of 4,6-disulfate, as well as larger fragments containing unsaturated glycosyl groups derived from L-idopyranosyluronic acid 2-sulfate, evidence of a relatively broad enzyme specificity. The presence of extra sulfate groups in dermatan sulfate did not enhance its weak antithrombotic activity, as measured by anti Xa, assay, in disagreement with earlier reports.