2,3,6-tri-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl]-α-D-glucopyranosyl isothiocyanate | 943860-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl]-α-D-glucopyranosyl isothiocyanate
• 英文别名: hepta-O-acetyl-α-D-maltosyl isothiocyanate；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-isothiocyanato-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 943860-91-1
• 化学式: C₂₇H₃₅NO₁₇S
• 分子量: 677.637
• InChiKey: ZEDXOYGZGOUVME-OTEFYFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  256
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl]-α-D-glucopyranosyl isothiocyanate 、 4-氟苯磺酰肼 以 乙腈 为溶剂， 以93.4%的产率得到
  参考文献：
  名称：

  Microwave and Ultrasound Irradiation‐Assisted Synthesis of Novel Disaccharide‐Derived Arylsulfonyl Thiosemicarbazides

  摘要：

  The synthesis of 1-arylsulfonyl-4-(1'-N-hepta-O-acetyl-ss- lactosyl) thiosemicarbazides by reaction of hepta-O-acetyl-alpha-D-lactosyl isothiocyanate with substituted phenylsulfonyl hydrazines has been shown to occur in less than 1 min under microwave activation and 8 min under ultrasound irradiation at room temperature. It is noteworthy that when ultrasound and microwaves (MW) were utilized, a cleaner reaction accompanied with higher yields was observed.

  DOI：

  10.1080/00397910600588249
• 作为产物：
  描述：

  Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 、 lead(II) thiocyanate 以 甲苯 为溶剂， 生成 2,3,6-tri-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl]-α-D-glucopyranosyl isothiocyanate
  参考文献：
  名称：

  Microwave and Ultrasound Irradiation‐Assisted Synthesis of Novel Disaccharide‐Derived Arylsulfonyl Thiosemicarbazides

  摘要：

  The synthesis of 1-arylsulfonyl-4-(1'-N-hepta-O-acetyl-ss- lactosyl) thiosemicarbazides by reaction of hepta-O-acetyl-alpha-D-lactosyl isothiocyanate with substituted phenylsulfonyl hydrazines has been shown to occur in less than 1 min under microwave activation and 8 min under ultrasound irradiation at room temperature. It is noteworthy that when ultrasound and microwaves (MW) were utilized, a cleaner reaction accompanied with higher yields was observed.

  DOI：

  10.1080/00397910600588249

文献信息

• Synthesis of α- and β-Glycosyl Isothiocyanates via Oxazoline Intermediates
  作者：José L. Jiménez Blanco、Balla Sylla、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/jo062419z

  日期：2007.6.1

  A practical synthesis of acylated glycosyl isothiocyanates from sugar oxazolines, by reaction with thiophosgene, is reported. In the absence of any additive, the reaction is governed by the reverse anomeric effect, leading to the equatorially oriented isothiocyanate. However, in the presence of copper(II) chloride, the reaction proceeds preferentially with retention of the configuration at the anomeric

  报道了通过与硫光气反应从糖恶唑啉实际合成酰化的糖基异硫氰酸酯。在不存在任何添加剂的情况下，该反应受反向异头作用的影响，从而导致赤道取向的异硫氰酸酯。然而，在氯化铜（II）的存在下，反应优选在构型保持在异头异构体中心处进行，从而提供轴向端基异构体作为主要产物。值得注意的是，该策略允许获得具有1,2-顺式相对构型（例如，d-葡萄糖和d-半乳糖系列中的α-端基异构体）的过-O-乙酰化的吡喃葡萄糖基异硫氰酸酯，此问题不在以前的方法学范围内。 。