2,3-O-methylidene-D-erythrono-1,4-lactone | 1106929-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2,3-O-methylidene-D-erythrono-1,4-lactone
• 英文别名: (3aR,6aR)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 1106929-66-1
• 化学式: C₅H₆O₄
• 分子量: 130.1
• InChiKey: CIXFPHPCHXUHHD-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-O-methylidene-D-erythrono-1,4-lactone 、 甲基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以81%的产率得到(3aR,6aR)-4-methyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ol
  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
• 作为产物：
  描述：

  二甲基亚砜 、 (3R,4R)-(-)-D-赤酮酸内酯 在 氯化亚砜 作用下， 反应 2.5h， 以70%的产率得到2,3-O-methylidene-D-erythrono-1,4-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

文献信息

• Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
  作者：Kathrine V. Booth、Filipa P. da Cruz、David J. Hotchkiss、Sarah F. Jenkinson、Nigel A. Jones、Alexander C. Weymouth-Wilson、Robert Clarkson、Thomas Heinz、George W.J. Fleet

  DOI：10.1016/j.tetasy.2008.10.013

  日期：2008.10

  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.