2-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)furan | 270924-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)furan
• 英文别名: (2S,3R,4R,5S)-2-(furan-2-yl)-6-methylidene-3,4,5-tris(phenylmethoxy)oxane
• CAS: 270924-32-8
• 化学式: C₃₁H₃₀O₅
• 分子量: 482.576
• InChiKey: YFDUYFLADQVSRR-VKONIRKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)furan 在 三异丁基铝 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.5h， 生成 2-[1D-(1,2,4,5/3)-2,3,4-tri-O-benzyl-5-O-methyl-2,3,4,5-tetrahydroxy-cyclohexyl]furan
  参考文献：
  名称：

  Synthesis of carba-β-d- and l-idopyranosides by rearrangement of unsaturated sugars

  摘要：

  The triisobutylaluminium- (TIBAL) and titanium(IV)-promoted conversions of 6-deoxyhex-5-enopyranosides into highly functionalised cyclohexane derivatives provide intermediates for the synthesis of enantiomerically pure carba-sugars. The preparation of enantiomerically pure methyl carba-beta-D-idopyranoside 1, methyl carba-beta-L-idopyranoside 2 and 5'a-carbadisaccharide 3 is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00479-6
• 作为产物：
  描述：

  1,6-二-O-乙酰基-2,3,4-三-O-苄基-beta-D-吡喃葡萄糖 在 咪唑 、 三氟甲磺酸三甲基硅酯 、 碘 、 sodium methylate 、 sodium hydride 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 4.5h， 生成 2-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)furan
  参考文献：
  名称：

  Synthesis of carba-β-d- and l-idopyranosides by rearrangement of unsaturated sugars

  摘要：

  The triisobutylaluminium- (TIBAL) and titanium(IV)-promoted conversions of 6-deoxyhex-5-enopyranosides into highly functionalised cyclohexane derivatives provide intermediates for the synthesis of enantiomerically pure carba-sugars. The preparation of enantiomerically pure methyl carba-beta-D-idopyranoside 1, methyl carba-beta-L-idopyranoside 2 and 5'a-carbadisaccharide 3 is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00479-6

文献信息

• Synthesis of carba-β-d- and l-idopyranosides by rearrangement of unsaturated sugars
  作者：Matthieu Sollogoub、Alan James Pearce、Alexandre Hérault、Pierre Sinaÿ

  DOI：10.1016/s0957-4166(99)00479-6

  日期：2000.1

  The triisobutylaluminium- (TIBAL) and titanium(IV)-promoted conversions of 6-deoxyhex-5-enopyranosides into highly functionalised cyclohexane derivatives provide intermediates for the synthesis of enantiomerically pure carba-sugars. The preparation of enantiomerically pure methyl carba-beta-D-idopyranoside 1, methyl carba-beta-L-idopyranoside 2 and 5'a-carbadisaccharide 3 is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.