2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetate | 383905-63-3

• 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-D-galactopyranosyl trichloroacetate
• 英文别名: trichloroacetyl 2,3,4,6-tetra-O-benzyl-D-galactopyranose；[(3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trichloroacetate
• CAS: 383905-63-3
• 化学式: C₃₆H₃₅Cl₃O₇
• 分子量: 686.029
• InChiKey: FYEWUXNMQOLHPM-BJPULKCASA-N

物化性质

• 沸点：
  720.1±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(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-D-galactopyranosyl trichloroacetate 在 molecular sieve 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 9.5h， 生成 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of a divalent glycoside of an α-galactosyl disaccharide epitope involved in the hyperacute rejection of xenotransplantation

  摘要：

  3,6-Dioxaoct-1,8-diyl di-(3-O-alpha -D-galactopyranosyl-beta -D-galactopyranoside) was synthesized for use in research on hyperacute rejection of xeno transplantation. The trichloroacetate method was successfully applied to form stereoselectively the a-D-galactosyl linkage under mild reaction conditions and a simple procedure. The divalent O-glycoside was formed from the corresponding trichloroacetimidate in one step with reasonable yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00194-x
• 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 1.5h， 以99%的产率得到2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetate
  参考文献：
  名称：

  Synthesis of a divalent glycoside of an α-galactosyl disaccharide epitope involved in the hyperacute rejection of xenotransplantation

  摘要：

  3,6-Dioxaoct-1,8-diyl di-(3-O-alpha -D-galactopyranosyl-beta -D-galactopyranoside) was synthesized for use in research on hyperacute rejection of xeno transplantation. The trichloroacetate method was successfully applied to form stereoselectively the a-D-galactosyl linkage under mild reaction conditions and a simple procedure. The divalent O-glycoside was formed from the corresponding trichloroacetimidate in one step with reasonable yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00194-x

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.