α-(3β)-cholest-5-en-3-yl-2,3,4,6-tetra-O-acetyl-D-glucopyranoside | 28154-13-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: α-(3β)-cholest-5-en-3-yl-2,3,4,6-tetra-O-acetyl-D-glucopyranoside
• 英文别名: cholest-5-en-3β-yl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；cholesteryl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranose；cholesteryl-(tetra-O-acetyl-α-D-glucopyranoside)；Cholesteryl-(tetra-O-acetyl-α-D-glucopyranosid)；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 28154-13-4
• 化学式: C₄₁H₆₄O₁₀
• 分子量: 716.953
• InChiKey: QAUUCWYBFGKUAM-TVAOKPRGSA-N

物化性质

• 熔点：
  188-190 °C
• 沸点：
  698.2±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  α-(3β)-cholest-5-en-3-yl-2,3,4,6-tetra-O-acetyl-D-glucopyranoside 在 溶剂黄146 、 铂 作用下， 生成 5α-cholestan-3β-yl-(tetra-O-acetyl-α-D-glucopyranoside)
  参考文献：
  名称：

  葡糖苷和β-1,3,4,6-四乙酰基葡萄糖aus三乙酰基葡聚糖-α1,2，β<1,5>

  摘要：

  DOI：

  10.1002/hlca.19480310148
• 作为产物：
  描述：

  β-(3β)-cholest-5-en-3-yl-2,3,4,6-tetra-O-acetyl-D-glucopyranoside 在 HgBr₂*HBr 作用下， 以 苯 为溶剂， 反应 3.0h， 以48%的产率得到α-(3β)-cholest-5-en-3-yl-2,3,4,6-tetra-O-acetyl-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of triterpene and steroid glycosides

  摘要：

  DOI：

  10.1016/s0008-6215(00)85361-6

文献信息

• de Pascual Teresa, Anales de la Real Sociedad Espanola de Fisica y Quimica, 1954, vol. <B> 50, p. 79,85
  作者：de Pascual Teresa

  DOI：——

  日期：——
• Nagarejan; Jagan Mohan Rao; Gunidutt, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 2, p. 132 - 134
  作者：Nagarejan、Jagan Mohan Rao、Gunidutt

  DOI：——

  日期：——
• Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger
  作者：Xiangying Gu、Lin Chen、Xin Wang、Xiao Liu、Qidong You、Wenwei Xi、Li Gao、Guohua Chen、Yue-Lei Chen、Bing Xiong、Jingkang Shen

  DOI：10.1021/jo402551x

  日期：2014.2.7

  A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-beta-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
• Synthesis of O- and S-glucosides using glucosyl halides and zinc salts
  作者：K Gurudutt

  DOI：10.1016/0008-6215(96)00011-0

  日期：1996.5.14
• Nishizawa, Mugio; Kan, Yukiko; Yamada, Hidetoshi, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 2, p. 565 - 567
  作者：Nishizawa, Mugio、Kan, Yukiko、Yamada, Hidetoshi

  DOI：——

  日期：——