methyl 2,4-di-O-methyl-fucopyranoside | 3006-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4-di-O-methyl-fucopyranoside
• 英文别名: O²,O⁴-dimethyl-D-6-deoxy-galactose；O²,O⁴-dimethyl-ξ-D-6-deoxy-galactopyranose；2.4-Di-O-methyl-D-fucose；2.4-Di-O-methyl-fucose；Labilose；Galactopyranose, 6-deoxy-2,4-di-O-methyl-, D-；(3R,4S,5R,6R)-3,5-dimethoxy-6-methyloxane-2,4-diol
• CAS: 3006-55-1
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: DEZVZPAUENCSBH-XLSKCSLXSA-N

物化性质

• 沸点：
  323.3±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.89
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4-di-O-methyl-fucopyranoside 在 sodium tetrahydroborate 作用下， 生成 2,4-di-O-methyl-6-deoxy-D-galactitol
  参考文献：
  名称：

  AKITA; MAEDA; UMEZAWA, Journal of Antibiotics, 1964, vol. 17, p. 200 - 215

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl O2,O4-dimethyl-α-D-6-deoxy-galactopyranoside 在 盐酸 作用下， 生成 methyl 2,4-di-O-methyl-fucopyranoside
  参考文献：
  名称：

  AKITA; MAEDA; UMEZAWA, Journal of Antibiotics, 1964, vol. 17, p. 200 - 215

  摘要：

  DOI：

文献信息

• Saponins of juk-siho and roots of Bupleurum longeradiatum Turcz.
  作者：HIROKO KIMATA、RYOJI KASAI、OSAMU TANAKA

  DOI：10.1248/cpb.30.4373

  日期：——

  In connection with our studies on the chemical evaluation of commercial Bupleuri Radix, isolation and identification of saponins of Juk-Siho (a Korean Bupleuri Radix) and roots of Bupleurum longeradiatum, the source plant of this crude drug, were carried out. From Juk-Siho, five saponins 1-5 were isolated. The saponins 1-3 were identified as saikosaponins-a (1), -c (2) and -d (3), respectively, all of which have already been isolated from roots of Bupleurum falcatum. The structures of the new saponins, named chikusaikosides-I (4) and -II (5), were estabished as 3-O-β-xylopyranosyl (1→2)-β-glucopyranosyl-(1→3)-β-fucopyranoside of saikogenin F (6) and 3-O-β-glucopyranosyl (1→6)-(α-rhamnopyranosyl (1→4)-β-glucopyranoside of 6, respectively. From roots of B. longeradiatum, saponins 1-4 were isolated and identified. During the course of the structure study of 4 by 13C-nuclear magnetic resonance (13C-NMR), an anomalous glycosylation shift for the 1, 2-linked glycoside was encountered.

  结合我们对商用柴胡的化学评估研究，我们对 Juk-Siho（一种韩国柴胡）和柴胡根（这种粗制药物的来源植物）的皂苷进行了分离和鉴定。从 Juk-Siho 中分离出五种皂苷 1-5。经鉴定，这些皂苷 1-3 分别为 saikosaponins-a (1)、-c (2) 和 -d (3)，所有这些皂苷都已从 Bupleurum falcatum 的根中分离出来。新皂甙的结构被确定为 3-O-β-xylopyranosyl-(1→2)-β-glucopyranosyl-(1→3)-β-fucopyranoside of saikogenin F (6) 和 3-O-β-glucopyranosyl (1→6)-(α-rhamnopyranosyl (1→4)-β-glucopyranoside of 6。从 B. longeradiatum 的根中分离并鉴定出了皂苷 1-4。在通过 13C 核磁共振（13C-NMR）对 4 的结构进行研究的过程中，发现 1，2-连接苷的糖基化转变异常。