4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-β-D-xylopyranoside | 475101-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-β-D-xylopyranoside
• 英文别名: allyl(-3)Gal2Ac4Ac6Ac(b1-4)Xyl(b)-O-Ph(4-OMe)；[(2R,3S,4S,5R,6R)-3,5-diacetyloxy-6-[(3R,4R,5R,6S)-4,5-dihydroxy-6-(4-methoxyphenoxy)oxan-3-yl]oxy-4-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 475101-59-8
• 化学式: C₂₇H₃₆O₁₄
• 分子量: 584.574
• InChiKey: QSDRYNCQCGGYSP-FRGVUBOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  175
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-β-D-xylopyranoside 在 (1,5-cyclooctadiene)(MePh₂P)2Ir*PF₆ 吡啶 、 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.75h， 生成 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
  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：

  tetra-O-acetyl-β-D-xylopyranose 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-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.