3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl-1-deoxy-1-thiocyanate | 127066-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl-1-deoxy-1-thiocyanate
• 英文别名: 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl thiocyanate；3,4,6-tri-O-acetyl-2-O-benzyl-1-thiocyano-β-D-glucopyranose；[(2R,3R,4S,5R,6S)-3,4-diacetyloxy-5-phenylmethoxy-6-thiocyanatooxan-2-yl]methyl acetate
• CAS: 127066-72-2
• 化学式: C₂₀H₂₃NO₈S
• 分子量: 437.471
• InChiKey: RVWXNZOZRNNDPY-OBKDMQGPSA-N

物化性质

• 熔点：
  110-111 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  554.9±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl-1-deoxy-1-thiocyanate 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl-3-O-(α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Kochetkov, N. K.; Klimov, E. M.; Malysheva, N. N., Doklady Chemistry, 1991, # 4-6, p. 393 - 396

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide 生成 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl-1-deoxy-1-thiocyanate
  参考文献：
  名称：

  KOCHETKOV, NIKOLAY K.;KLIMOV, EVGENY M.;MALYSHEVA, NELLY N., TETRAHEDRON LETT., 30,(1989) N0, C. 5459-5462

  摘要：

  DOI：

文献信息

• Synthesis of polysaccharides with 1,2-cis-glycosidic linkages by tritylthiocyanate polycondensation. Stereoregular α-(1-6)-D-glucan
  作者：Nikolay K. Kochetkov、Nelly N. Malysheva、Evgeny M. Klimov、Alexey V. Demchenko

  DOI：10.1016/s0040-4039(00)74137-2

  日期：1992.1

  The completely stereoregular polysaccharide, α-(1-6)-D-glucan, has been synthesised using a new highly stereospecific type of polycondensation process - trityl-thiocyanate polycondensation.

  完全立体有规的多糖，α-（1-6）-D-葡聚糖，是使用一种新型的高度立体有规的缩聚工艺合成的，即三苯甲基硫氰酸酯缩聚。
• On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides
  作者：Sophon Kaeothip、Steven J. Akins、Alexei V. Demchenko

  DOI：10.1016/j.carres.2010.08.003

  日期：2010.10

  Comparative side-by-side glycosylation studies demonstrated that glycosyl thiocyanates, thioimidates, and thioglycosides provide comparative stereoselectivities in glycosylations. Very high alpha-stereoselectivity that was previously recorded for glycosyl thiocyanates can be achieved, but only if glycosyl acceptors are equipped with electron-withdrawing acyl substituents. Partially benzylated glycosyl acceptors provided relatively modest stereoselectivity, which was on a par with other common glycosyl donors. Accordingly, thioimidates and thioglycosides showed high stereoselectivity similarly to that of thiocyanates with different classes of acylated primary and secondary glycosyl acceptors. (C) 2010 Elsevier Ltd. All rights reserved.
• A new stereospecific method for 1,2-cis-glycosylation
  作者：Nicolay K. Kochetkov、Evgeny M. Klimov、Nelly N. Malysheva、Alexey V. Demchenko

  DOI：10.1016/0008-6215(91)84047-i

  日期：1991.6

  A new stereospecific method for 1,2-cis-glycosylation involves the reaction of 1,2-trans-glycosyl thiocyanates with sugar trityl ethers in the presence of triphenylmethylium perchlorate, The method has been applied to give disaccharide derivatives with (1 --> 6), (1 --> 4),(1 --> 3), and (1 --> 2) linkages.
• Demchenko, A.V.; Malysheva, N.N.; Kochetkov, N.K., Doklady Chemistry, 1995, vol. 341, # 4-6, p. 121 - 123
  作者：Demchenko, A.V.、Malysheva, N.N.、Kochetkov, N.K.

  DOI：——

  日期：——
• Kochetkov, N.K.; Malysheva, N.N.; Klimov, E.M., Doklady Chemistry, 1991, vol. 320, # 1-3, p. 274 - 277
  作者：Kochetkov, N.K.、Malysheva, N.N.、Klimov, E.M.、Demchenko, A.V.

  DOI：——

  日期：——