2,3,4,6-四-O-乙酰基-1-氯-Β-D-甘露糖 | 14227-52-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,3,4,6-四-O-乙酰基-1-氯-Β-D-甘露糖
• 中文别名: 2,3,3',4,5-五氯联苯
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride
• 英文别名: tetra-O-acetyl-β-D-mannopyranosyl chloride；2,3,4,6-Tetra-O-acetyl-D-mannopyranosyl chloride；tetra-O-acetyl-β-D-mannopyranosyl chloride；Tetra-O-acetyl-β-D-mannopyranosylchlorid；2,3,4,6-Tetra-O-acetyl-β-D-manno-pyranosylchlorid；2,3,4,6-Tetraacetoxy-β-D-mannopyranosyl-chlorid；[(2R,3R,4S,5S,6S)-3,4,5-Triacetyloxy-6-chlorooxan-2-yl]methyl acetate
• CAS: 14227-52-2
• 化学式: C₁₄H₁₉ClO₉
• 分子量: 366.752
• InChiKey: BYWPSIUIJNAJDV-PEBLQZBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-O-乙酰基-1-氯-Β-D-甘露糖 在 四丁基碘化铵 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 Ethyl N-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-thiocarbamate
  参考文献：
  名称：

  A New Procedure for the Synthesis of Glycosyl Isothiocyanates

  摘要：

  DOI：

  10.1055/s-1984-30885
• 作为产物：
  描述：

  D-甘露糖 、 乙酰氯 在 indium(III) triflate 作用下， 反应 3.0h， 以80%的产率得到2,3,4,6-四-O-乙酰基-1-氯-Β-D-甘露糖
  参考文献：
  名称：

  Indium(III) Triflate–Mediated One-Step Preparation of Glycosyl Halides from Free Sugars

  摘要：

  In(OTf)3 has been found to be an efficient catalyst for the direct conversion of reducing sugars to their respective acylated glycosyl halides in good yields under mild conditions. The glycosyl halides so obtained can be converted to alkyl glycosides in the same pot by reacting them with the respective alcohols in good yield.

  DOI：

  10.1080/00397910903419886

文献信息

• Synthesis of glycosyl chlorides using catalytic Appel conditions
  作者：Imlirenla Pongener、Kirill Nikitin、Eoghan M. McGarrigle

  DOI：10.1039/c9ob01544b

  日期：——

  stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly

  描述了使用催化Appel条件立体选择性合成糖基氯。使用一定范围的糖基半缩醛，草酰氯和5 mol％的Ph3PO，可获得高产率的α-糖基氯。对于2-脱氧糖，在没有氧化膦催化剂的情况下用草酰氯处理相应的半缩醛也得到了良好的糖基氯收率。该方法操作简单，并且可以容易地除去5mol％的氧化膦副产物。或者，可以进行一锅多催化剂糖基化以将糖基半缩醛直接转化为糖苷。
• 128. Preparation and properties of some poly-O-acetylglycosyl chlorides of the “unstable” series
  作者：W. Korytnyk、J. A. Mills

  DOI：10.1039/jr9590000636

  日期：——
• Photohalogenation of glycopyranosyl halides: An expedient route to c-1 gem dihalogenated sugars
  作者：Jean-Pierre Praly、Laurent Brard、Gérard Descotes、Loīc Toupet

  DOI：10.1016/s0040-4020(01)81310-7

  日期：1989.1
• NOVEL SYNTHESIS OF 1-THIOGLYCOPYRANOSES VIA THIOIMINIUM SALTS
  作者：Takayoshi Fujihira、Mitsutaka Chida、Haruo Kamijo、Toshio Takido、Manabu Seno

  DOI：10.1081/car-120013495

  日期：2002.9.23

  Methanolysis of a glycosylthioiminium salt, which was prepared from the reaction of acetohalogenosugar with thioacetamide, afforded the corresponding per-O-acetylated 1,2-trans-1-thioglycose in good yield after fractional crystallization. This synthetic method is very convenient in operation and proceeds without loss of acetyl groups, as the reaction is carried out under mild and neutral conditions.
• Chretien, Francoise; Cesare, Pierre Di; Gross, Bernard, Journal of the Chemical Society. Perkin transactions I, 1988, p. 3297 - 3300
  作者：Chretien, Francoise、Cesare, Pierre Di、Gross, Bernard

  DOI：——

  日期：——