4-methoxyphenyl O-[(methyl 2,3,4-tri-O-(4-methylbenzoyl)-β-D-glucopyranosid)uronate]-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside | 943977-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl O-[(methyl 2,3,4-tri-O-(4-methylbenzoyl)-β-D-glucopyranosid)uronate]-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside
• CAS: 943977-41-1
• 化学式: C₈₃H₈₈O₃₃
• 分子量: 1613.59
• InChiKey: SSEWTNWVUKNSHT-LCPCCMCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  116.0
• 可旋转键数：
  28.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  398.67
• 氢给体数：
  0.0
• 氢受体数：
  33.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl O-[(methyl 2,3,4-tri-O-(4-methylbenzoyl)-β-D-glucopyranosid)uronate]-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.5h， 以93%的产率得到
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  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.

  DOI：

  10.1080/07328300701296810
• 作为产物：
  描述：

  methyl (2,3,4-tri-O-4-methylbenzoyl-α-D-glucopyranosyl trichloroacetimidate)uronate 、 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 以32%的产率得到4-methoxyphenyl O-[(methyl 2,3,4-tri-O-(4-methylbenzoyl)-β-D-glucopyranosid)uronate]-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  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.

  DOI：

  10.1080/07328300701296810

文献信息

• Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin
  作者：Jun-ichi Tamura、Akihiro Yamaguchi、Junko Tanaka

  DOI：10.1016/s0960-894x(02)00327-x

  日期：2002.8

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.