methyl (methyl 6-deoxy-2,3-O-isopropylidene-5-oxo-β-D-ribo-heptafuranosid)uronate | 566198-49-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl (methyl 6-deoxy-2,3-O-isopropylidene-5-oxo-β-D-ribo-heptafuranosid)uronate
• 英文别名: methyl 3-[(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-3-oxopropanoate
• CAS: 566198-49-0
• 化学式: C₁₂H₁₈O₇
• 分子量: 274.271
• InChiKey: DZBGPRPQPFKWTE-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (methyl 6-deoxy-2,3-O-isopropylidene-5-oxo-β-D-ribo-heptafuranosid)uronate 在 盐酸 、 (S)-BinapRuBr₂ 、 氢气 、 镍 、 zinc methyl bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~40.0 ℃ 、101.33 kPa 条件下， 反应 91.5h， 生成 methyl (methyl 6-deoxy-2,3-O-isopropylidene-6-[(N-benzhydryl-N-methyl)amino]-D-glycero-β-D-allo-heptafuranosid)uronate
  参考文献：
  名称：

  Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins

  摘要：

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00460-x
• 作为产物：
  描述：

  2,3-邻异亚丙基-1-邻甲基-D-核糖酸 、 magnesium monomethyl malonate 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 以60%的产率得到methyl (methyl 6-deoxy-2,3-O-isopropylidene-5-oxo-β-D-ribo-heptafuranosid)uronate
  参考文献：
  名称：

  Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins

  摘要：

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00460-x

文献信息

• Asymmetric hydrogenations of glycoside derived β-ketoesters
  作者：C. Thomassigny、C. Greck

  DOI：10.1016/j.tetasy.2003.11.001

  日期：2004.1

  The catalytic hydrogenation of beta-ketoesters bearing a sugar moiety at C-3 is reported. Hydrogenations in the presence of chiral ruthenium(II) complexes are highly diastereoselective. The hydrogenation stereoselectivity of the ribose derived beta-ketoester was controlled by the catalyst. The C-5 substituent of the xylose derived beta-ketoester influenced the stereochemical course of the catalytic hydrogenation: the diastereoselectivity was controlled by the substrate if the C-5 substituent is a bulky group. (C) 2003 Published by Elsevier Ltd.
• Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins
  作者：Bruno Drouillat、Olivia Poupardin、Yann Bourdreux、Christine Greck

  DOI：10.1016/s0040-4039(03)00460-x

  日期：2003.3

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthetic route towards (5R,2′S,5′S,6′S)-ribosyl-diazepanone, an analogue core of the liposidomycins
  作者：Bruno Drouillat、Yann Bourdreux、Delphine Perdon、Christine Greck

  DOI：10.1016/j.tetasy.2007.07.023

  日期：2007.8

  The synthesis of (5R,2'S,5'S,6'S)-ribosyl-diazepanone, an analogue core of liposidomycins is described. The core ribosyl seven-membered heterocycle of nucleoside antibiotic liposidomycins was formed by reductive amination of an alpha-ribosylamino ester derived from D-ribose, and an amino aldehyde derived from methyl 4-triisopropylsilyloxy-3-oxobutanoate, followed by a peptidic coupling reaction. (c) 2007 Elsevier Ltd. All rights reserved.