[(2R,3S,4R)-4-acetyloxy-5-methoxy-2-[(4-methylphenyl)sulfonyloxymethyl]oxolan-3-yl] acetate | 266688-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R)-4-acetyloxy-5-methoxy-2-[(4-methylphenyl)sulfonyloxymethyl]oxolan-3-yl] acetate
• CAS: 266688-14-6
• 化学式: C₁₇H₂₂O₉S
• 分子量: 402.422
• InChiKey: BTSZIVSTTZIUMJ-LVYZTWJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R)-4-acetyloxy-5-methoxy-2-[(4-methylphenyl)sulfonyloxymethyl]oxolan-3-yl] acetate 在 Dowex AG-50W-H₈ (H(+) form) 、 Dowex AG-50W-X₈ (H(+) form) sodium hydroxide 、 水 、 焦磷酸硫胺素 、 Lithium hydroxypyruvate 、 sodium iodide 、 magnesium chloride 、 锌 作用下， 以 乙醚 、 水 、 异丙醇 为溶剂， 反应 108.67h， 生成 5,6-dideoxy-D-arabino-hept-5-en-2-ulose
  参考文献：
  名称：

  Substrate specificity and carbohydrate synthesis using transketolase

  摘要：

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.

  DOI：

  10.1021/jo00048a023
• 作为产物：
  描述：

  异恶唑，3-isocyanato-5-(1-methylethyl)-(9CI) 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 [(2R,3S,4R)-4-acetyloxy-5-methoxy-2-[(4-methylphenyl)sulfonyloxymethyl]oxolan-3-yl] acetate
  参考文献：
  名称：

  Substrate specificity and carbohydrate synthesis using transketolase

  摘要：

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.

  DOI：

  10.1021/jo00048a023

文献信息

• Nanomolar versus Millimolar Inhibition by Xylobiose-Derived Azasugars:  Significant Differences between Two Structurally Distinct Xylanases
  作者：Spencer J. Williams、Roland Hoos、Stephen G. Withers

  DOI：10.1021/ja993805j

  日期：2000.3.1

  deoxynojirimycin (Ki = 5800 nM) derivatives of xylobiose. By contrast, none of the compounds inhibited the family 11 xylanase, Bcx, from Bacillus circulans, to an appreciable extent. Two possible explanations are provided for the discrimination exhibited by the imidazole and the lactam oxime. One explanation relates to the different active site locations of the acid/base residue in the two enzymes: anti to

  描述了木二糖衍生的含氮木聚糖酶抑制剂的合成，从可获得的前体开始，通过有效的合成方案。四种双糖被鉴定为来自纤维单胞菌的保留家族 10 木聚糖酶 Cex 的强大竞争抑制剂，即咪唑 (Ki = 150 nM)、内酰胺肟 (Ki = 370 nM)、异发米 (Ki = 130 nM) 和脱氧野尻霉素 ( Ki = 5800 nM) 木二糖衍生物。相比之下，没有一种化合物在明显程度上抑制来自环状芽孢杆菌的家族 11 木聚糖酶 Bcx。对咪唑和内酰胺肟表现出的区别提供了两种可能的解释。一种解释与两种酶中酸/碱残基的不同活性位点位置有关：10 Cex 家族的 C1-O5 键和 11 Bcx 家族的 Syn 键。另一种解释涉及两种酶的过渡态构象的拟议差异：Cex 的半椅和 Bcx 的船。这...