3,4-O-methylidene-2-C-methyl-D-arabinono-1,5-lactone | 936338-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 3,4-O-methylidene-2-C-methyl-D-arabinono-1,5-lactone
• 英文别名: 2-C-Methyl-3,4-O-methylidene-D-arabinono-1,5-lactone；(3aR,7S,7aR)-7-hydroxy-7-methyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 936338-38-4
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: YNJPPLXATLKDEI-XAHCXIQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  sodium cyanide 、 (3aR,6aR)-4-methyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ol 在 Amberlite IR 120 (H⁺) 作用下， 以 水 为溶剂， 反应 66.0h， 以15%的产率得到3,4-O-methylidene-2-C-methyl-D-arabinono-1,5-lactone
  参考文献：
  名称：

  Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone

  摘要：

  Readily crystallized 2-C-methyl-D-ribono-1,4-lactone is formed in a one-pot procedure from D-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-L-ribono-1,4-lactone is similarly produced from L-glucose. 3,4-O-Isopropylidene-2-C-methyl-D-arabinono-1,5-lactone and 2-C-methyl-D-arabinono-1,4-lactone were prepared in a combined 60% yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-D-ribulose derived from D-erythronolactone; the enantiomeric arabinonolactones are similarly available from L-erythronolactone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.013