2,3,4,6-tetra-O-acetyl-1-S-(Z)-(2-naphthhydroximoyl)-1-thio-β-D-galactopyranose | 854602-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3,4,6-tetra-O-acetyl-1-S-(Z)-(2-naphthhydroximoyl)-1-thio-β-D-galactopyranose
• CAS: 854602-98-5
• 化学式: C₂₅H₂₇NO₁₀S
• 分子量: 533.556
• InChiKey: OOJUWWMVXNWBPL-DOUVXQEGSA-N

物化性质

• 熔点：
  93-95 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• 沸点：
  655.8±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  147.02
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-S-(Z)-(2-naphthhydroximoyl)-1-thio-β-D-galactopyranose 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.67h， 生成 (5S,6R,7S,8R,9R)-9-(hydroxymethyl)-3-naphthalen-2-yl-1,10-dioxa-4-thia-2-azaspiro[4.5]dec-2-ene-6,7,8-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 、 N-hydroxy-2-naphthimidoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到2,3,4,6-tetra-O-acetyl-1-S-(Z)-(2-naphthhydroximoyl)-1-thio-β-D-galactopyranose
  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