2-propyl 3-deoxy-4-S-(β-D-galactopyranosyl)-4-thio-α-D-xylo-hexopyranoside | 1191092-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propyl 3-deoxy-4-S-(β-D-galactopyranosyl)-4-thio-α-D-xylo-hexopyranoside
• 英文别名: benzyl 3-deoxy-4-S-(β-D-galactopyranosyl)-4-thio-β-threo-pentopyranoside；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(3S,5S,6R)-5-hydroxy-6-phenylmethoxyoxan-3-yl]sulfanyloxane-3,4,5-triol
• CAS: 1191092-94-0
• 化学式: C₁₈H₂₆O₈S
• 分子量: 402.466
• InChiKey: XCAXFAYZOFLGOH-MWVUGINQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S)-2-benzyloxy-2H-pyran-3(6H)-one 在 水 、 potassium tri-sec-butyl-borohydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-propyl 3-deoxy-4-S-(β-D-galactopyranosyl)-4-thio-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthesis of pentopyranosyl-containing thiodisaccharides. Inhibitory activity against β-glycosidases

  摘要：

  beta-(1 -> 4)-Thiodisaccharides formed by a pentopyranose unit as reducing or non reducing end have been synthesized using a sugar enone derived from a hexose or pentose as Michael acceptor of a 1-thiopentopyranose or 1-thiohexopyranose derivatives. Thus, 2-propyl per-O-acetyl-3-deoxy-4-S-(beta-D-Xylp)-4-thiohexopyranosid-2-ulose (3) and benzyl per-O-acetyl-3-deoxy-4-S-(beta-D-Galp)-4-thiopentopyranosid-2-ulose (11) were obtained in almost quantitative yields. The carbonyl function of these uloses was reduced with NaBH4 or K-Selectride, and the stereochemical course of the reduction was highly dependent on the reaction temperature, reducing agent and solvent. Unexpectedly, reduction of 3 with NaBH4-THF at 0 degrees C gave a 3-deoxy-4-S-(beta-D-Xylp)-4-thio-alpha-D-ribo-hexopyranoside derivative (6) as major product (74% yield), with isomerization of the sulfur-substituted C-4 stereocenter of the pyranone. Reduction of 11 gave always as major product the benzyl 3-deoxy-4-S-(Galp)-4-thio-beta-D-threo-pentopyranoside derivative 14, which was the only product isolated (80% yield) in the reduction with K-Selectride in THF at -78 degrees C. Deprotection of 14 and its epimer at C-2 (13) afforded, respectively the free thiodisaccharides 19 and 18. They displayed strong inhibitory activity against the beta-galactosidase from Escherichia coli. Thus, compound 18 proved to be a non-competitive inhibitor of the enzyme (K-i = 0.80 mM), whereas 19 was a mixed-type inhibitor (K-i = 32 mu M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.055

文献信息

• Synthesis of pentopyranosyl-containing thiodisaccharides. Inhibitory activity against β-glycosidases
  作者：Alejandro J. Cagnoni、María Laura Uhrig、Oscar Varela

  DOI：10.1016/j.bmc.2009.07.055

  日期：2009.9.1

  beta-(1 -> 4)-Thiodisaccharides formed by a pentopyranose unit as reducing or non reducing end have been synthesized using a sugar enone derived from a hexose or pentose as Michael acceptor of a 1-thiopentopyranose or 1-thiohexopyranose derivatives. Thus, 2-propyl per-O-acetyl-3-deoxy-4-S-(beta-D-Xylp)-4-thiohexopyranosid-2-ulose (3) and benzyl per-O-acetyl-3-deoxy-4-S-(beta-D-Galp)-4-thiopentopyranosid-2-ulose (11) were obtained in almost quantitative yields. The carbonyl function of these uloses was reduced with NaBH4 or K-Selectride, and the stereochemical course of the reduction was highly dependent on the reaction temperature, reducing agent and solvent. Unexpectedly, reduction of 3 with NaBH4-THF at 0 degrees C gave a 3-deoxy-4-S-(beta-D-Xylp)-4-thio-alpha-D-ribo-hexopyranoside derivative (6) as major product (74% yield), with isomerization of the sulfur-substituted C-4 stereocenter of the pyranone. Reduction of 11 gave always as major product the benzyl 3-deoxy-4-S-(Galp)-4-thio-beta-D-threo-pentopyranoside derivative 14, which was the only product isolated (80% yield) in the reduction with K-Selectride in THF at -78 degrees C. Deprotection of 14 and its epimer at C-2 (13) afforded, respectively the free thiodisaccharides 19 and 18. They displayed strong inhibitory activity against the beta-galactosidase from Escherichia coli. Thus, compound 18 proved to be a non-competitive inhibitor of the enzyme (K-i = 0.80 mM), whereas 19 was a mixed-type inhibitor (K-i = 32 mu M). (C) 2009 Elsevier Ltd. All rights reserved.