2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetate | 155500-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetate
• 英文别名: 2,3,4,6-tetra-benzyl-1-O-trichloroacetyl-α-D-galactopyranose；[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trichloroacetate
• CAS: 155500-50-8
• 化学式: C₃₆H₃₅Cl₃O₇
• 分子量: 686.029
• InChiKey: FYEWUXNMQOLHPM-BWNLSPMZSA-N

物化性质

• 沸点：
  720.1±60.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetate 、 苯甲醇 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 反应 2.0h， 以83%的产率得到1,2,3,4,6-pentabenzyl-D-galactose
  参考文献：
  名称：

  Studies on Glycosides XIV. Stereoselectivity and Reactivity of New C1 Leaving Group Trichloroacetoxyl in Glycosylation Reaction

  摘要：

  2,3,4,6-O-Tetrabenzyl-1-alpha-D-galactopyransyl trichloroacete (2) reacted with a series of nucleophiles in the presence of BF3 . OEt(2) or TMSOTf to give O-, S-galactopyranosides and galactopyranosyl carboxylates stereoselectively in high yields.

  DOI：

  10.1080/00397919508011769
• 作为产物：
  描述：

  2,3,4,6-四-O-苄基-D-吡喃半乳糖 、 三氯乙酸酐 在 sodium trichloroacetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetate
  参考文献：
  名称：

  Studies on Glycosides XIV. Stereoselectivity and Reactivity of New C1 Leaving Group Trichloroacetoxyl in Glycosylation Reaction

  摘要：

  2,3,4,6-O-Tetrabenzyl-1-alpha-D-galactopyransyl trichloroacete (2) reacted with a series of nucleophiles in the presence of BF3 . OEt(2) or TMSOTf to give O-, S-galactopyranosides and galactopyranosyl carboxylates stereoselectively in high yields.

  DOI：

  10.1080/00397919508011769

文献信息

• Sequential one-pot glycosylation with glycosyl N-trichloroacetylcarbamate and trichloroacetate including dehydrative approach using 1-hydroxy sugars
  作者：Tatsuya Shirahata、Asami Kojima、Satoko Teruya、Jun-ichi Matsuo、Masaki Yokoyama、Shogo Unagiike、Toshiaki Sunazuka、Kazuishi Makino、Eisuke Kaji、Satoshi Ōmura、Yoshinori Kobayashi

  DOI：10.1016/j.tet.2011.06.006

  日期：2011.9

  An efficient sequential one-pot glycosylation has been developed with glycosyl trichlorocarbamate and trichloroacetate activated by the same Lewis acid and enabled by a change in reaction temperature. The act-selective glycosylation was achieved using glucose, galactose, and mannose substrates after investigation into the reactivities of the two types of glycosyl donors. Sequential one-pot dehydrative glycosylation, including in situ preparation of glycosyl donors followed by generation of two glycosyl bonds, provided three types of trisaccharide. (C) 2011 Published by Elsevier Ltd.
• Studies on Glycosides XIV. Stereoselectivity and Reactivity of New C1 Leaving Group Trichloroacetoxyl in Glycosylation Reaction
  作者：Jianmin Mao、Hongming Chen、Jian Zhang、Mengshen Cai

  DOI：10.1080/00397919508011769

  日期：1995.5

  2,3,4,6-O-Tetrabenzyl-1-alpha-D-galactopyransyl trichloroacete (2) reacted with a series of nucleophiles in the presence of BF3 . OEt(2) or TMSOTf to give O-, S-galactopyranosides and galactopyranosyl carboxylates stereoselectively in high yields.