methyl α-galactopyranoside 6-sulfate | 117858-45-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-galactopyranoside 6-sulfate
• 英文别名: methyl α-D-galactoside 6-sulfate；methyl α-D-galactopyranoside；methyl-(O⁶-sulfo-α-D-galactopyranoside)；Methyl-(O⁶-sulfo-α-D-galactopyranosid)；Methyl-β-D-galactopyranosid-6-sulfat；[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl hydrogen sulfate
• CAS: 117858-45-4
• 化学式: C₇H₁₄O₉S
• 分子量: 274.249
• InChiKey: YWICHBRKRCIFIH-PZRMXXKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl α-galactopyranoside 6-sulfate 在 barium dihydroxide 、 水 作用下， 生成 甲基3,6-脱水-ALPHA-D-半乳糖苷
  参考文献：
  名称：

  148.碳水化合物硫酸酯。第二部分 从甲基己吡喃糖苷硫酸盐中分离出3：6-脱水甲基己糖苷

  摘要：

  DOI：

  10.1039/jr9410000830
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 吡啶 、 chlorosulphuric acid 、 氯仿 作用下， 生成 methyl α-galactopyranoside 6-sulfate
  参考文献：
  名称：

  273.碳水化合物硫酸酯。第一部分葡萄糖和半乳糖硫酸盐

  摘要：

  DOI：

  10.1039/jr9400001475

文献信息

• Regioselectivity in Sulfation of Galactosides by Sulfuric Acid and Dicyclobexylcarbodi-imide
  作者：Ryo Takano、Takashi Ueda、Yasuhide Uejima、Kaeko Kamel-Hayashi、Saburo Hara、Susumu Hirase

  DOI：10.1271/bbb.56.1413

  日期：1992.1

  Methyl α- and β-D-galactopyranosides and 4-O-β-D-galactopyranosyl-3,6-anhydro-L-galactose dimethylacetal were sulfated with sulfuric acid and dicyclohexylcarbodi-imide as a condensation reagent. The sulfated sugars were isolated by ion-exchange chromatography, characterized, and assigned by methylation analyses. On the basis of the yield of each sulfated product that was isolated, sulfation on O-6 appeared to be predominant.

  甲基α-和β-D-半乳糖吡喃苷及4-O-β-D-半乳糖吡喃苷-3,6-去水-L-半乳糖二甲基缩醛在硫酸和二环己基碳二亚胺的作用下进行了硫酸化。硫酸化的糖通过离子交换色谱法分离，进行了表征，并通过甲基化分析进行了鉴定。根据分离出的每种硫酸化产物的产率，O-6上的硫酸化似乎占主导地位。
• PROCESS FOR PRODUCING DESULFATED POLYSACCHARIDE, AND DESULFATED HEPARIN
  申请人：SEIKAGAKU CORPORATION

  公开号：EP0769502A1

  公开（公告）日：1997-04-23

  This invention relates to a process for producing a desulfated polysaccharide, which comprises reacting a sulfated polysaccharide having a saccharide in which a primary hydroxyl group is sulfated, as a constituent sugar, with a silylating agent represented by the following formula (I) wherein R1s are the same or different and each represent a hydrogen atom or a halogen atom, R2 represents a lower alkyl group, and R3s are the same or different and each represent a lower alkyl group, an aryl group or a halogen atom, and a desulfated heparin obtained by this production process.

  本发明涉及一种生产脱硫多糖的工艺，该工艺包括将硫酸化多糖与硅烷化剂进行反应，硅烷化剂由下式（I）表示，硫酸化多糖的组成糖是一种初级羟基被硫酸化的糖。 其中 R1s 相同或不同，各自代表氢原子或卤素原子；R2 代表低级烷基；R3s 相同或不同，各自代表低级烷基、芳基或卤素原子、 以及通过该生产工艺获得的脱硫肝素。
• Process for producing desulfated polysaccharide, and desulfated heparin
  申请人：SEIKAGAKU CORPORATION

  公开号：US20030149253A1

  公开（公告）日：2003-08-07

  This invention relates to a process for producing a desulfated polysaccharide, which comprises reacting a sulfated polysaccharide having a saccharide in which a primary hydroxyl group is sulfated, as a constituent sugar, with a silylating agent represented by the following formula (I) 1 wherein R 1 s are the same or different and each represent a hydrogen atom or a halogen atom, R 2 represents a lower alkyl group, and R 3 s are the same or different and each represent a lower alkyl group, an aryl group or a halogen atom, and a desulfated heparin obtained by this production process.

  本发明涉及一种生产脱硫多糖的工艺，该工艺包括将硫酸化多糖与硅烷化剂进行反应，硅烷化剂由下式(I)代表，硫酸化多糖的组成糖是一个伯羟基被硫酸化的糖类。 1 其中 R 1 s 相同或不同，且各自代表氢原子或卤素原子，R 2 代表低级烷基，而 R 3 s相同或不同，各自代表低级烷基、芳基或卤素原子、 以及通过该生产工艺获得的脱硫肝素。
• Takano, Ryo; Matsuo, Masayoshi; Kamei-Hayashi, Kaeko, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 10, p. 1577 - 1580
  作者：Takano, Ryo、Matsuo, Masayoshi、Kamei-Hayashi, Kaeko、Hara, Saburo、Hirase, Susumu

  DOI：——

  日期：——
• Is Sulfate Lost During the Chemical Release of Oligosaccharides from Glycoproteins?
  作者：Kevin R. King、J. Michael Williams、John R. Clamp、Anthony P. Corfield

  DOI：10.1080/07328309608005423

  日期：1996.1

  Model experiments using methyl alpha-D-galactopyranoside 6-sulfate have implied that the Carlson conditions (1 M sodium borohydride and 0.05 M sodium hydroxide at 45 degrees C) for the release of O-linked oligosaccharides from glycoproteins do not cause significant loss of sulfate ester groups. However the more vigorous conditions used to release N-linked oligosaccharides are more likely to cause considerable sulfate loss from a galactoside 6-sulfate as a result of 3,6-anhydride formation. Experiments with dextran sulfate suggested that sulfate loss due to oxirane formation was also not significant under the Carlson conditions. These results were supported by experiments with [S-35]sulfate-labelled human rectal mucus glycoprotein.