3,4,6-tri-O-benzyl-β-D-galactopyranosyl fluoride | 112289-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,6-tri-O-benzyl-β-D-galactopyranosyl fluoride
• 英文别名: 3,4,6-tri-O-benzyl-beta-D-galactopyranosyl fluoride；(2S,3R,4R,5S,6R)-2-fluoro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 112289-35-7
• 化学式: C₂₇H₂₉FO₅
• 分子量: 452.523
• InChiKey: SQGDIWBZBSPKMC-IURCNINISA-N

物化性质

• 沸点：
  584.8±50.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-β-D-galactopyranosyl fluoride 在 silver perchlorate 、 sodium hydride 、 tin(ll) chloride 、 2,4-di-tert-butyl-6-methylpyridine 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 3,4-di-O-benzyl-6-O-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol
  参考文献：
  名称：

  2-Deoxy-disaccharide approach to natural and unnatural glycosphingolipids synthesis

  摘要：

  2-Deoxy-disaccharides were easily converted into glycosylphytosphingosines, as new and efficient precursors of natural and unnatural glycosphingolipids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00366-9
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-1,2-O-ethylidene-α-D-galactopyranose 在 盐酸 、 硫酸 、 potassium tert-butylate 、 silver fluoride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 乙醚 、 乙腈 、 苯 为溶剂， 反应 20.0h， 生成 3,4,6-tri-O-benzyl-β-D-galactopyranosyl fluoride
  参考文献：
  名称：

  取代的2,7-二氧杂双环[4.1.0]庚烷的合成：1,2-脱水-3,4,6-三-O-苄基和1,2-脱水-3,4,6-三-O- （对溴苄基）-α-d-吡喃半乳糖

  摘要：

  摘要由d-半乳糖经9个步骤合成了标题化合物。为了获得稳定的1，2-嵌段的d-吡喃半乳糖醚，用亚乙基而不是1-乙氧基亚乙基保护1，2-羟基。合成的关键中间体是2-O-乙酰基-3,4,6-三-O-苄基和2-O-乙酰基-3,4,6-三-O-（对溴苄基）-β- d-吡喃半乳糖基氟是由相应的，被氟化银取代的α-d-吡喃半乳糖基氯制备的。用叔丁醇钾在环戊烷中回流下定量测定β-d-吡喃半乳糖基氟的闭环，得到结晶的目标化合物。合成中涉及的大多数反应容易以高产率进行。

  DOI：

  10.1016/0008-6215(87)80217-3

文献信息

• METHOD OF SYNTHESIZING SUGAR CHAIN
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1640379A1

  公开（公告）日：2006-03-29

  An object of the present invention is to provide a method for efficiently chemically synthesizing biomolecules including a nucleotide (nucleic acid), a peptide (protein), or a sugar chain, as representative examples. The present invention provides a method of solid-phase synthesis of sugar chain(s) for synthesizing multiple types of sugar chains in at least one sugar chain synthesis reaction system comprising multiple types of monosaccharide units, which is characterized in that it comprises changing the temperature in the sugar chain synthesis reaction system depending on the temperature rising rate that has been determined based on a decrease in side reaction(s) in the reaction system as an indicator.

  本发明的目的是提供一种有效地化学合成生物分子的方法，包括核苷酸（核酸）、肽（蛋白质）或糖链等代表性示例。本发明提供了一种固相合成糖链的方法，用于在至少一个糖链合成反应系统中合成多种类型的糖链，其特征在于根据已确定的反应系统中副反应减少的指标，改变糖链合成反应系统中的温度上升速率。
• Method for synthesizing sugar chain(s)
  申请人：Kanie Osamu

  公开号：US20060166278A1

  公开（公告）日：2006-07-27

  An object of the present invention is to provide a method for efficiently chemically synthesizing biomolecules including a nucleotide (nucleic acid), a peptide (protein), or a sugar chain, as representative examples. The present invention provides a method of solid-phase synthesis of sugar chain(s) for synthesizing multiple types of sugar chains in at least one sugar chain synthesis reaction system comprising multiple types of monosaccharide units, which is characterized in that it comprises changing the temperature in the sugar chain synthesis reaction system depending on the temperature rising rate that has been determined based on a decrease in side reaction(s) in the reaction system as an indicator.

  本发明的目的是提供一种高效地化学合成生物分子的方法，包括核苷酸（核酸）、肽（蛋白质）或糖链等代表性分子。本发明提供了一种固相合成糖链的方法，用于在至少一个糖链合成反应系统中合成多种类型的糖链，该反应系统包含多种单糖单元，其特征在于根据反应系统中副反应的减少作为指标确定的温度升高速率来改变糖链合成反应系统中的温度。
• Synthesis of a library of fucopyranosyl-galactopyranosides consisting of a complete set of anomeric configurations and linkage positions
  作者：Isao Ohtsuka、Takuro Ako、Rumiko Kato、Shusaku Daikoku、Satomi Koroghi、Takuya Kanemitsu、Osamu Kanie

  DOI：10.1016/j.carres.2006.03.040

  日期：2006.7

  A library composed of a complete set of fucopyranosyl-galactopyranosides was synthesized. A perbenzylated phenylthio fucopyranoside and a series of tri-O-benzyl-galactopyranosyl fluorides having single hydroxyl groups at the 2-, 3-, 4-, and 6-positions were used as the glycosyl donor and glycosyl acceptors, respectively. The chosen set of functionalities at the anomeric centers enabled rapid access to the oligosaccharides based on chemoselective activation. The first coupling reaction was achieved by the action of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST). The resulting disaccharide fluoride was readily activated by hafnocene bistrifluoromethanesulfonate [Cp2Hf(OTf)(2)] and glycosidated with n-octanol. (c) 2006 Elsevier Ltd. All rights reserved.
• 2-Deoxy-disaccharide approach to natural and unnatural glycosphingolipids synthesis
  作者：Andrea Graziani、Pietro Passacantilli、Giovanni Piancatelli*、Simona Tani

  DOI：10.1016/s0957-4166(00)00366-9

  日期：2000.10

  2-Deoxy-disaccharides were easily converted into glycosylphytosphingosines, as new and efficient precursors of natural and unnatural glycosphingolipids. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of substituted 2,7-dioxabicyclo[4.1.0]heptanes: 1,2-anhydro-3,4,6-tri-O-benzyl- and 1,2-anhydro-3,4,6-tri-O-(p-bromobenzyl)-α-d-galactopyranose
  作者：Fanzuo Kong、Jingying Du、Heng Shang

  DOI：10.1016/0008-6215(87)80217-3

  日期：1987.5

  1,2-blocked d -galactopyranose ethers, the 1,2-hydroxyl groups were protected with an ethylidene group instead of a 1-ethoxyethylidene group. The key intermediates for the synthesis were 2- O -acetyl-3,4,6-tri- O -benzyl- and 2- O -acetyl-3,4,6-tri- O -( p -bromobenzyl)-β- d -galactopyranosyl fluoride that were prepared from the corresponding, substituted α- d -galactopyranosyl chlorides with silver

  摘要由d-半乳糖经9个步骤合成了标题化合物。为了获得稳定的1，2-嵌段的d-吡喃半乳糖醚，用亚乙基而不是1-乙氧基亚乙基保护1，2-羟基。合成的关键中间体是2-O-乙酰基-3,4,6-三-O-苄基和2-O-乙酰基-3,4,6-三-O-（对溴苄基）-β- d-吡喃半乳糖基氟是由相应的，被氟化银取代的α-d-吡喃半乳糖基氯制备的。用叔丁醇钾在环戊烷中回流下定量测定β-d-吡喃半乳糖基氟的闭环，得到结晶的目标化合物。合成中涉及的大多数反应容易以高产率进行。