methyl 6-deoxy-6-fluoro-α-D-galactopyranoside | 4536-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-fluoro-α-D-galactopyranoside
• 英文别名: methyl-[6-fluoro-α-D-fucopyranoside；Methyl-[6-fluor-α-D-fucopyranosid；(2S,3R,4S,5R,6S)-2-(fluoromethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 4536-13-4
• 化学式: C₇H₁₃FO₅
• 分子量: 196.176
• InChiKey: SCFXAGHFILDGHI-PZRMXXKTSA-N

物化性质

• 沸点：
  339.5±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-fluoro-α-D-galactopyranoside 在 水 、 三氟乙酸 作用下， 反应 5.0h， 以76%的产率得到6-deoxy-6-fluorogalactose
  参考文献：
  名称：

  UDP-6-deoxy-6-fluoro-α-d-galactose binds to two different galactosyltransferases, but neither can effectively catalyze transfer of the modified galactose to the appropriate acceptor

  摘要：

  The effect of substitution of the HO-6 of D-galactose with fluorine on the ability of alpha-(1 --> 3)-galactosyltransferase (EC 2.4.1.151) and beta-(1 --> 4)-galactosyltransferase (EC 2.4.1.22) to catalyze its transfer from UDP to an appropriate acceptor was determined. HPLC analyses indicated that each transferase properly catalyzed formation of the expected product [beta-D-Gal-(1 --> 4)-D-GlcNAc for the beta-(1 --> 4)-galactosyltransferase and alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 --> 4)-D-GlcNAc for the alpha-(1 --> 3)-D-galactosyltransferase] when UDP-alpha-D-Gal was the substrate. When UDP-6-deoxy-6-fluoro-alpha-D-galactose (6) was used in conjunction with each transferase, no product indicative of transfer of 6-deoxy-6-fluoro-D-galactose to its respective acceptor sugar was identified. 6-Deoxy-6-fluoro-D-galactose (3) was obtained by hydrolysis of methyl 6-deoxy-6-fluoro-alpha-D-galactopyranoside, synthesized by the selective fluorination of methyl alpha-D-galactopyranoside with diethylaminosulfur trifluoride (DAST), with aqueous trifluoroacetic acid. Acetylation of 3 gave crystalline 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-beta-D-galactopyranose, which was converted to the corresponding 1-alpha-phosphate and used for the synthesis of 6. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00104-4
• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-α-D-galactopyranoside 在 吡啶 、 水 、 乙二醇 、 溶剂黄146 、 cesium fluoride 作用下， 反应 8.0h， 生成 methyl 6-deoxy-6-fluoro-α-D-galactopyranoside
  参考文献：
  名称：

  甲基α-D-吡喃半乳糖苷衍生物的6位氟化。

  摘要：

  DOI：

  10.1016/0008-6215(94)84202-7

文献信息

• 168. Fluorocarbohydrates. Part I. The synthesis of 6-deoxy-6-fluoro-α-<scp>D</scp>-galactose and 5-deoxy-5-fluoro-αβ-<scp>D</scp>-ribose
  作者：N. F. Taylor、P. W. Kent

  DOI：10.1039/jr9580000872

  日期：——
• UDP-6-deoxy-6-fluoro-α-d-galactose binds to two different galactosyltransferases, but neither can effectively catalyze transfer of the modified galactose to the appropriate acceptor
  作者：Cara-Lynne Schengrund、Pavol Kováč

  DOI：10.1016/s0008-6215(99)00104-4

  日期：1999.6

  The effect of substitution of the HO-6 of D-galactose with fluorine on the ability of alpha-(1 --> 3)-galactosyltransferase (EC 2.4.1.151) and beta-(1 --> 4)-galactosyltransferase (EC 2.4.1.22) to catalyze its transfer from UDP to an appropriate acceptor was determined. HPLC analyses indicated that each transferase properly catalyzed formation of the expected product [beta-D-Gal-(1 --> 4)-D-GlcNAc for the beta-(1 --> 4)-galactosyltransferase and alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 --> 4)-D-GlcNAc for the alpha-(1 --> 3)-D-galactosyltransferase] when UDP-alpha-D-Gal was the substrate. When UDP-6-deoxy-6-fluoro-alpha-D-galactose (6) was used in conjunction with each transferase, no product indicative of transfer of 6-deoxy-6-fluoro-D-galactose to its respective acceptor sugar was identified. 6-Deoxy-6-fluoro-D-galactose (3) was obtained by hydrolysis of methyl 6-deoxy-6-fluoro-alpha-D-galactopyranoside, synthesized by the selective fluorination of methyl alpha-D-galactopyranoside with diethylaminosulfur trifluoride (DAST), with aqueous trifluoroacetic acid. Acetylation of 3 gave crystalline 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-beta-D-galactopyranose, which was converted to the corresponding 1-alpha-phosphate and used for the synthesis of 6. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Fluorination at position 6 of derivatives of methyl α-d-galactopyranoside
  作者：Laurence A. Mulard、P. Kováč、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(94)84202-7

  日期：1994.6