methyl (2,3,4-tri-O-4-methylbenzoyl-α-D-glucopyranosyl trichloroacetimidate)uronate | 145661-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3,4-tri-O-4-methylbenzoyl-α-D-glucopyranosyl trichloroacetimidate)uronate
• CAS: 145661-89-8
• 化学式: C₃₃H₃₀Cl₃NO₁₀
• 分子量: 706.961
• InChiKey: SERNXCYYADDTGK-XXPVTOLNSA-N

物化性质

• 沸点：
  734.8±70.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  47.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  147.51
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl (2,3,4-tri-O-4-methylbenzoyl-α-D-glucopyranosyl trichloroacetimidate)uronate 在 吡啶 、 4-二甲氨基吡啶 、 MS-AW₃₀₀ 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 、 苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis of sulfated glycohexaose of linkage region of chondroitin 4-sulfate: β-D-GlcA-(1→3){(SO3Na→4)}-β-D-GalNAc-(1→4)-β-D-GlcA-(1→3)-β-D-Gal-(1→3 )-β-D-Gal-(1→4)-D-Xyl

  摘要：

  Stereocontrolled synthesis of glycohexaoses 3 and 4 which corresponds to the linkage region of chondroitin 4-sulfate to a core protein was achieved for the first time by employing glycotriosyl donor 5 and glycotriosyl acceptor 6.

  DOI：

  10.1016/s0040-4039(00)61790-2
• 作为产物：
  描述：

  1,2,3,4-四-O-乙酰基-Β-D-葡萄糖醛酸甲酯 在 吡啶 、 sodium methylate 、 四氯化锡 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 methyl (2,3,4-tri-O-4-methylbenzoyl-α-D-glucopyranosyl trichloroacetimidate)uronate
  参考文献：
  名称：

  Synthesis of sulfated glycohexaose of linkage region of chondroitin 4-sulfate: β-D-GlcA-(1→3){(SO3Na→4)}-β-D-GalNAc-(1→4)-β-D-GlcA-(1→3)-β-D-Gal-(1→3 )-β-D-Gal-(1→4)-D-Xyl

  摘要：

  Stereocontrolled synthesis of glycohexaoses 3 and 4 which corresponds to the linkage region of chondroitin 4-sulfate to a core protein was achieved for the first time by employing glycotriosyl donor 5 and glycotriosyl acceptor 6.

  DOI：

  10.1016/s0040-4039(00)61790-2

文献信息

• Synthetic approach towards sulfated chondroitin di-, tri- and tetrasaccharides corresponding to the repeating unit
  作者：Jun-ichi Tamura、Klaus W Neumann、Sadamu Kurono、Tomoya Ogawa

  DOI：10.1016/s0008-6215(97)00225-5

  日期：1997.12

  Chondroitin di-, tri- and tetrasaccharides, as well as their 4-, 6-mono- and 4,6-disulfates as their 4-methoxyphenyl glycosides, were systematically synthesized. Target disaccharides having beta GalNAc-(1-->4)-beta GlcA sequences were obtained starting from the corresponding pivotal chondroitin disaccharide precursor. A trisaccharide intermediate, which was synthesized by coupling of glucuronate imidate

  系统合成了软骨素二，三和四糖，以及它们的4-，6-单-和4,6-二硫酸盐作为它们的4-甲氧基苯基糖苷。从相应的关键性软骨素二糖前体开始获得具有βGalNAc-（1→4）-βGlcA序列的目标二糖。通过将葡萄糖醛酸亚氨酸酯与已知的二糖受体偶联而合成的三糖中间体被转化为硫酸化和非硫酸化软骨素三糖。软骨素四糖和相应的4-二硫酸盐，6-二硫酸盐以及4,6-四硫酸盐也是基于上述开发的策略而获得的，从已报道的具有[βGalN3-（1→4）-βGlcA2]的四糖开始顺序。
• Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase
  作者：Jun‐ichi Tamura、Akihiro Yamaguchi、Junko Tanaka、Yuko Nishimura

  DOI：10.1080/07328300701296810

  日期：2007.4.30

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.
• Synthesis of β-GlcA-(1→3)-β-Gal and α-GalNAc-(1→4)-β-GleA-(1→3)-β-Gal as Biotinylated 2-Aminoethyl Glycoside and the Streptavidin Complex Formation
  作者：Jun-ichi Tamura、Yoshiaki Miura、Hudson H. Freeze

  DOI：10.1080/07328309908543974

  日期：1999.1.1