1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose | 214001-50-0

• 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: 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose
• 英文别名: 1-[(4aS,6R,7R,8S,8aS)-3-methyl-7,8-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiin-2-yl]ethanone
• CAS: 214001-50-0
• 化学式: C₃₂H₃₄O₆S
• 分子量: 546.684
• InChiKey: AXWGFRIGTHQRCM-CWGIXRCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose 在 sodium tetrahydroborate 、 4 A molecular sieve 、 苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 (Z)-3-[(2S,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl]sulfanylpent-3-en-2-one
  参考文献：
  名称：

  10.1002/(sici)1099-0690(199908)1999:8<1869::aid-ejoc1869<3.0.co;2-a

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199908)1999:8<1869::aid-ejoc1869<3.0.co;2-a
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 、 3-thiophthalimide-2,4-pentanedione 在 2,6-二甲基吡啶 、 3 Angstroem MS 作用下， 以 二甲基亚砜 为溶剂， 反应 168.0h， 以42%的产率得到1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose
  参考文献：
  名称：

  Novel Heterocycloaddition Reaction of Glycals

  摘要：

  Diacyl thione species 1 has been generated and reacted in situ with both pyranoid and furanoid glycals to form novel [4 + 2] cycloadducts. Factors such as protecting groups and configuration of substituents in the glycals along with medium effects were varied to discover influences on face selectivity and reactivity. A qualitative correlation of reactivity with the HOMO-LUMO gap between the glycal (HOMO) and the heterodienic species (LUMO) is observed. In one example, the isolation of byproducts suggests that the cycloaddition may in fact be stepwise.

  DOI：

  10.1021/jo981047u

文献信息

• 10.1002/(sici)1099-0690(199908)1999:8<1869::aid-ejoc1869<3.0.co;2-a
  作者：Dios, Angeles、Nativi, Cristina、Capozzi, Giuseppe、Franck, Richard W.

  DOI：10.1002/(sici)1099-0690(199908)1999:8<1869::aid-ejoc1869<3.0.co;2-a

  日期：——
• Novel Heterocycloaddition Reaction of Glycals
  作者：Angeles Dios、Aloma Geer、Cecilia H. Marzabadi、Richard W. Franck

  DOI：10.1021/jo981047u

  日期：1998.9.1

  Diacyl thione species 1 has been generated and reacted in situ with both pyranoid and furanoid glycals to form novel [4 + 2] cycloadducts. Factors such as protecting groups and configuration of substituents in the glycals along with medium effects were varied to discover influences on face selectivity and reactivity. A qualitative correlation of reactivity with the HOMO-LUMO gap between the glycal (HOMO) and the heterodienic species (LUMO) is observed. In one example, the isolation of byproducts suggests that the cycloaddition may in fact be stepwise.