O²-benzyl-O³,O⁴-isopropyliden-1,6-anhydro-β-D-galactopyranose | 55287-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: O²-benzyl-O³,O⁴-isopropyliden-1,6-anhydro-β-D-galactopyranose
• 英文别名: (1R,2S,6S,7R,8R)-4,4-dimethyl-7-phenylmethoxy-3,5,9,11-tetraoxatricyclo[6.2.1.02,6]undecane
• CAS: 55287-62-2
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: GWSSDPGTTFIYIY-GZBLMMOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O²-benzyl-O³,O⁴-isopropyliden-1,6-anhydro-β-D-galactopyranose 在 氢溴酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl bromide
  参考文献：
  名称：

  Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells

  摘要：

  Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of alpha-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An alpha-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of alpha-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in alpha-galactosylceramides influences cytokine release profiles.

  DOI：

  10.1021/ja045385q
• 作为产物：
  描述：

  1,-脱水-3,-O-异丙二烯-β-D-谷氨酸五乙酸酯 在 氨 、 sodium 作用下， 生成 O²-benzyl-O³,O⁴-isopropyliden-1,6-anhydro-β-D-galactopyranose
  参考文献：
  名称：

  4-苄基-2,3-异亚丙基-d-甘露聚糖（1.5）β（1,6）和2-苄基-3,4-异亚丙基-d-半乳糖苷（1,5）β（1,6）。

  摘要：

  DOI：

  10.1021/ja01183a600

文献信息

• Sarbajna, Sumita; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 3, p. 252 - 256
  作者：Sarbajna, Sumita、Roy, Nirmolendu

  DOI：——

  日期：——
• Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells
  作者：Randal D. Goff、Ying Gao、Jochen Mattner、Dapeng Zhou、Ning Yin、Carlos Cantu、Luc Teyton、Albert Bendelac、Paul B. Savage

  DOI：10.1021/ja045385q

  日期：2004.10.1

  Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of alpha-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An alpha-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of alpha-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in alpha-galactosylceramides influences cytokine release profiles.
• New Compounds. 4-Benzyl-2,3-isopropylidene-D-mannosan<1,5>β<1,6> and 2-Benzyl-3,4-isopropylidene-D-galactosan<1,5>β<1,6>
  作者：W Haskins、Raymond Hann、C Hudson

  DOI：10.1021/ja01183a600

  日期：1948.3