Chloro-acetic acid (3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-tetrahydro-pyran-3-yl ester | 147242-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Chloro-acetic acid (3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-tetrahydro-pyran-3-yl ester
• CAS: 147242-30-6
• 化学式: C₈H₁₃ClO₆
• 分子量: 240.641
• InChiKey: OASVBOBNXRWFFG-PXBUCIJWSA-N

物化性质

• 沸点：
  358.7±42.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.14
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-tetrahydro-pyran-3-yl ester 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 硫脲 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside
  参考文献：
  名称：

  A practical synthesis of β-d-GlcA-(1→3)-β-d-Gal-(1→3)-β-d-Gal-(1→4)-d-Xyl, a part of the common linkage region of a glycosaminoglycan

  摘要：

  A practical synthesis of beta-D-GlcA-(1 --> 3)-beta-D-Gal-(1 --> 3)-beta-D-Gal-(1 -->4)-beta-D-Xyl-(1 --> OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-beta-D-xylopyranoside, followed by deallylation. The beta-(1 --> 3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside as the key synthon. The alpha-(1--> 3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation. CO 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00169-6
• 作为产物：
  描述：

  氯乙酰氯 、 甲基-β-D-吡喃木糖苷 在 二正丁基氧化锡 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 Chloro-acetic acid (3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A practical synthesis of β-d-GlcA-(1→3)-β-d-Gal-(1→3)-β-d-Gal-(1→4)-d-Xyl, a part of the common linkage region of a glycosaminoglycan

  摘要：

  A practical synthesis of beta-D-GlcA-(1 --> 3)-beta-D-Gal-(1 --> 3)-beta-D-Gal-(1 -->4)-beta-D-Xyl-(1 --> OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-beta-D-xylopyranoside, followed by deallylation. The beta-(1 --> 3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside as the key synthon. The alpha-(1--> 3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation. CO 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00169-6