β-D-Glucosaccharino-1,4-lacton | 7306-56-1

• 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: β-D-Glucosaccharino-1,4-lacton
• 英文别名: 2-C-methyl-L-arabinono-1,4-lactone；(3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one
• CAS: 7306-56-1
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: WJBVKNHJSHYNHO-RVJQKOHUSA-N

物化性质

• 沸点：
  338.3±11.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-D-Glucosaccharino-1,4-lacton 、 苯肼 生成 2-C-Methyl-L-arabonsaeure-phenylhydrazid
  参考文献：
  名称：

  支链糖。第八部分 对2- C-甲基-L-阿拉伯糖和-核糖化学的贡献

  摘要：

  用重氮甲烷处理甲基3,4- O-异亚丙基-β - L-赤型-戊硫吡喃糖苷，然后用氢化铝锂处理，得到两种异构的2- C-甲基戊糖苷衍生物：优势产物具有核糖构型。提供了支持分配给产品的配置的证据。定性地比较了2- C-甲基-L-核糖和-阿拉伯糖在酸性和碱性介质中的稳定性与L-阿拉伯糖和D-核糖的稳定性。处理甲基2,2'-脱水-2- C-羟甲基-3,4 - O的初步结果注意到-异亚丙基-β - L-戊苷（阿拉伯糖和核糖异构体的混合物）与甲醇氨。

  DOI：

  10.1039/j39680001091
• 作为产物：
  描述：

  sodium cyanide 、 (3aS,6aS)-2,2,4-trimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ol 以 水 为溶剂， 生成 β-D-Glucosaccharino-1,4-lacton 、 3,4-O-isopropylidene-2-C-methyl-L-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

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.
• Branched-chain sugars. Part VIII. A contribution to the chemistry of 2-C-methyl-L-arabinose and -ribose
  作者：R. J. Ferrier、W. G. Overend、G. A. Rafferty、H. M. Wall、N. R. Williams

  DOI：10.1039/j39680001091

  日期：——

  Treatment of methyl 3,4-O-isopropylidene-β-L-erythro-pentosulopyranoside with diazomethane followed by lithium aluminium hydride yields two isomeric 2-C-methylpentoside derivatives: the preponderant product has the ribo-configuration. Evidence to support the configurations assigned to the products is provided. The stabilities of 2-C-methyl-L-ribose and -arabinose in acidic and basic media have been

  用重氮甲烷处理甲基3,4- O-异亚丙基-β - L-赤型-戊硫吡喃糖苷，然后用氢化铝锂处理，得到两种异构的2- C-甲基戊糖苷衍生物：优势产物具有核糖构型。提供了支持分配给产品的配置的证据。定性地比较了2- C-甲基-L-核糖和-阿拉伯糖在酸性和碱性介质中的稳定性与L-阿拉伯糖和D-核糖的稳定性。处理甲基2,2'-脱水-2- C-羟甲基-3,4 - O的初步结果注意到-异亚丙基-β - L-戊苷（阿拉伯糖和核糖异构体的混合物）与甲醇氨。