Acetic acid (5S,7R,8S,9S,10R)-8,9-diacetoxy-7-acetoxymethyl-3-(4-bromo-phenyl)-1,6-dioxa-4-thia-2-aza-spiro[4.5]dec-2-en-10-yl ester | 854602-96-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (5S,7R,8S,9S,10R)-8,9-diacetoxy-7-acetoxymethyl-3-(4-bromo-phenyl)-1,6-dioxa-4-thia-2-aza-spiro[4.5]dec-2-en-10-yl ester
• CAS: 854602-96-3
• 化学式: C₂₁H₂₂BrNO₁₀S
• 分子量: 560.376
• InChiKey: JKVACHHIZNMZCL-CWVBCOCOSA-N

物化性质

• 沸点：
  581.6±60.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  136.02
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (5S,7R,8S,9S,10R)-8,9-diacetoxy-7-acetoxymethyl-3-(4-bromo-phenyl)-1,6-dioxa-4-thia-2-aza-spiro[4.5]dec-2-en-10-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以69%的产率得到(5S,7R,8R,9S,10R)-3-(4-Bromo-phenyl)-7-hydroxymethyl-1,6-dioxa-4-thia-2-aza-spiro[4.5]dec-2-ene-8,9,10-triol
  参考文献：
  名称：

  β-d-Galactopyranosyl-thiohydroximates and d-galactopyranosylidene-spiro-oxathiazoles: synthesis and enzymatic evaluation against E. colid-galactosidase

  摘要：

  By reaction with arylhydroximoyl chlorides, 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranose was converted to the corresponding beta-D-galactopyranosyl-thiohydroximates, which gave predominantly (1S)-D-galactopyranosylidene-spiro-oxathiazoles on illumination in the presence of NBS. Conventional O-deacetylation of both thiohydroximates and oxathiazoles gave weak inhibitors of E. coli D-galactosidase (K-i 1.1-11.1 mM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.021
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-硫代-BETA-D-吡喃半乳糖 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 Acetic acid (5S,7R,8S,9S,10R)-8,9-diacetoxy-7-acetoxymethyl-3-(4-bromo-phenyl)-1,6-dioxa-4-thia-2-aza-spiro[4.5]dec-2-en-10-yl ester
  参考文献：
  名称：

  β-d-Galactopyranosyl-thiohydroximates and d-galactopyranosylidene-spiro-oxathiazoles: synthesis and enzymatic evaluation against E. colid-galactosidase

  摘要：

  By reaction with arylhydroximoyl chlorides, 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranose was converted to the corresponding beta-D-galactopyranosyl-thiohydroximates, which gave predominantly (1S)-D-galactopyranosylidene-spiro-oxathiazoles on illumination in the presence of NBS. Conventional O-deacetylation of both thiohydroximates and oxathiazoles gave weak inhibitors of E. coli D-galactosidase (K-i 1.1-11.1 mM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.02.021