methyl 2,3-di-O-benzyl-4-O-crotonyl-6-deoxy-α-D-glucopyranoside | 250687-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-4-O-crotonyl-6-deoxy-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-6-methoxy-2-methyl-4,5-bis(phenylmethoxy)oxan-3-yl] (E)-but-2-enoate
• CAS: 250687-53-7
• 化学式: C₂₅H₃₀O₆
• 分子量: 426.51
• InChiKey: AZXSGNHTAKIBNL-QOGZCOGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-4-O-crotonyl-6-deoxy-α-D-glucopyranoside 在 氢氧化钾 、 copper(I) bromide dimethylsulfide complex 、 二甲基硫 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.17h， 生成 methyl 6-deoxy-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Highly Stereoselective 1,4-Conjugate Addition of Organocopper Reagents to Methyl α-d-Glucopyranoside Derivatives Tethering an Unsaturated Ester Moiety at C-4 or C-6¹

  摘要：

  [GRAPHICS]The 1,4-conjugate additions of a variety of organocopper reagents to some 4-O-crotonyl derivatives of methyl alpha-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a beta-substituted butanoic ester at C-4, The 1,4-conjugate addition to a 6-O-crotonyl derivative afforded the adduct with reverse configuration at the beta-carbon to that obtained from the 4-O-crotonyl derivatives.

  DOI：

  10.1021/ol9909942
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside 生成 methyl 2,3-di-O-benzyl-4-O-crotonyl-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Highly Stereoselective 1,4-Conjugate Addition of Organocopper Reagents to Methyl α-d-Glucopyranoside Derivatives Tethering an Unsaturated Ester Moiety at C-4 or C-6¹

  摘要：

  [GRAPHICS]The 1,4-conjugate additions of a variety of organocopper reagents to some 4-O-crotonyl derivatives of methyl alpha-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a beta-substituted butanoic ester at C-4, The 1,4-conjugate addition to a 6-O-crotonyl derivative afforded the adduct with reverse configuration at the beta-carbon to that obtained from the 4-O-crotonyl derivatives.

  DOI：

  10.1021/ol9909942

文献信息

• Highly Diastereoselective 1,4-Addition of an Organocuprate to Methyl α-<scp>d</scp>-Gluco-, α-<scp>d</scp>-Manno-, or α-<scp>d</scp>-Galactopyranosides Tethering an α,β-Unsaturated Ester. Novel Asymmetric Access to β-C-Substituted Butanoic Acids
  作者：Kiichiro Totani、Takayuki Nagatsuka、Shuhei Yamaguchi、Ken-ichi Takao、Shigeru Ohba、Kin-ichi Tadano

  DOI：10.1021/jo0101860

  日期：2001.9.1

  yields. Other organocuprates also serve as effective carbon nucleophiles for the 1,4-addition. Removal of the carbohydrate moiety from each adduct afforded a variety of beta-C-substituted butanoic esters in remarkable enantiomeric excess. The 1,4-addition of the same cuprate to some methyl alpha-D-manno- or alpha-D-galactopyranosidic substrates in which a crotonyl group was incorporated, each at 3-OH

  由乙烯基溴化镁和溴化亚铜制备的1，4-二乙烯基铜镁酸加到甲基α-D-吡喃葡萄糖苷的一些4-O-巴豆酰基衍生物中，可以高水平地进行非对映化学诱导，从而提供了良好至优异收率的加合物。其他有机铜酸盐也可作为有效的碳亲核试剂用于1,4-加成。从每个加合物中除去碳水化合物部分，得到了各种对映体过量的β-C-取代的丁酸酯。还研究了相同的铜酸盐在一些甲基α-D-甘露聚糖或α-D-吡喃半乳糖苷底物中的1，4-加成，每个底物中并入了巴豆酰基，各自在3-OH上。当某些D-甘露聚糖类型的底物经受1，4-添加条件类似于用于D-葡萄糖型底物的条件。此外，一些D-半乳糖型底物提供具有更高非对映选择性的1，4-加合物。
• Munakata, Ryosuke; Totani, Kiichiro; Takao, Ken-Ichi, Synlett, 2000, # 7, p. 979 - 982
  作者：Munakata, Ryosuke、Totani, Kiichiro、Takao, Ken-Ichi、Tadano, Kin-Ichi

  DOI：——

  日期：——