O-[2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl]trichloroacetimidate | 113421-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-[2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl]trichloroacetimidate
• 英文别名: O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate；[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 113421-48-0
• 化学式: C₄₀H₅₂Cl₃NO₂₆
• 分子量: 1069.2
• InChiKey: UHZSSMWBPZCUTD-CRCSEORLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  70.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  342.23
• 氢给体数：
  1.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  O-[2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl]trichloroacetimidate 在 3 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2S,3R,4E)-2-azido-3-hydroxyoctadec-4-enyl (α-D-galactopyranosyl)-(1->4)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  globotriosylceramide的一些糖苷配基类似物的合成

  摘要：

  通过将合适的官能化的醇与过乙酰化的球三糖三氯乙酰亚胺酸酯进行糖基化反应，合成七种globotriosylceramide的糖苷配基类似物，然后进一步转化糖苷配基并去除保护基。

  DOI：

  10.1016/s0008-6215(99)00230-x
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 O-[2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl]trichloroacetimidate
  参考文献：
  名称：

  Synthesis of some divalent O- and S-glycosides of galabiose and globotriose

  摘要：

  Derivatives of galabiose (alpha-D-Galp-(1-->4)-D-Galp) and globotriose (alpha-D-Galp-(1-->4)-beta-D-Galp(1-->4)-D-Glcp) were coupled to various 1,2- and 1,3-dihydroxymethyl- and dimercaptomethylbenzenes to give the corresponding divalent glycosides, potentially useful as inhibitors of bacterial adhesion. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00021-4

文献信息

• Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide
  作者：Katsuya Koike、Mamoru Sugimoto、Susumu Sato、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/0008-6215(87)80181-7

  日期：1987.6

  Stereoselective, total synthesis of O-alpha-D-galactopyranosyl-(1----4) -O-beta-D-galactopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----1)-N -tetracosanoyl-[2S,3R,4E (and 4Z)]-sphingenine and O-alpha-D -galactopyranosyl-(1----3)-O-beta-D-galactopyranosyl-(1----4)-O-beta-D -glucopyranosyl-(1----1)-N-tetracosanoyl-(2S,3R,4E)-sphin gen ine was achieved by using O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)

  O-α-D-吡喃半乳糖基-（1 ---- 4）-O-β-D-吡喃半乳糖基-（1 ---- 4）-O-β-D-吡喃葡萄糖基-（1-的立体选择性全合成--- 1）-N-十四烷酰基-[2S，3R，4E（和4Z）]-鞘氨醇和O-α-D-吡喃半乳糖基-（1 ---- 3）-O-β-D-吡喃半乳糖基-（通过使用O-（2,3）可实现1 ---- 4）-O-β-D-吡喃葡萄糖基-（1 ---- 1）-N-十四烷酰基-（2S，3R，4E）-斯宾碱，4,6-四-O-乙酰基-α-D-吡喃半乳糖基）-（1 ---- 4）-O-（2,3,6-三-O-乙酰基-β-D-吡喃半乳糖基）-（ 1 ---- 4）-2,3,6-三-O-乙酰基-α-D-吡喃葡萄糖基三氯乙酰亚氨酸酯，O-（2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基） -（1 ---- 4）-O-（2,3,6-三-O-乙酰基-β-D-吡喃半乳糖基）-（1
• Qiu, Dongxu; Schmidt, Richard R., Liebigs Annalen der Chemie, 1992, # 3, p. 217 - 224
  作者：Qiu, Dongxu、Schmidt, Richard R.

  DOI：——

  日期：——
• Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents
  作者：Mohamed R.E. Aly、Pascal Rochaix、Mohamed Amessou、Ludger Johannes、Jean-Claude Florent

  DOI：10.1016/j.carres.2006.03.044

  日期：2006.9

  The galactosyl donor, 4,6-di-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyl trichloroacetimidate, was efficiently coupled with regioselectively benzylated lactoside acceptors under standard conditions to stereoselectively afford the corresponding globotrioside and isoglobotrioside derivatives in very good yields. These glycosides were smoothly functionalized with a 6-(p-cinnamoylplienoxy)-hexyl tether tag as novel electrophilic thiol-specific carbohydrate reagents. Immobilization of the globotrioside conjugate to Thiopropyl Sepharose 6B for purification of B-subunit of Shiga toxin (StxB) and coupling of a model cysteine-containing protein (StxB-Z(n)-Cys) to the isoglobotrioside conjugate were both performed with high efficiency. (c) 2006 Elsevier Ltd. All rights reserved.
• Silicon nitride sugar chips for detection of Ricinus communis proteins and Escherichia coli O157 Shiga toxins
  作者：Daiki Tanaka、Hirotaka Uzawa、Takehiro Nagatsuka、Yuki Oba、Atsunori Hiratsuka、Ken-ichi Tayama、Toshio Yoshida、Yasuo Seto、Hirofumi Dohi、Yoshihiro Nishida

  DOI：10.1016/j.ab.2019.06.002

  日期：2019.9

  Lactosides having either an amino-triethylene glycol or an azido-triethylene glycol were designed and synthesized, and the two derivatives were immobilized onto silicon nitride (SiN) surfaces. When a click reaction was applied for the immobilization of the azido-sugar, a Ricinus commons lectin (RCA(120)) was detected with a higher response by reflectometric interference spectroscopy (RIfS). When an N-hydroxysuccinimide (NHS) method was applied for the sugar immobilization, the response was less than that of the click one. The response of bovine serum albumin (BSA) as the negative control was negligible, but the lactose-SiN chip prepared by the click method suppressed nonspecific binding more effectively than did the chip from the NHS method. Next, we examined an antibody-immobilized SiN chip prepared by the click reaction. The detection response was, however, lower than that of the lactose-SiN chip, meaning that the sugar-chip by the click reaction was superior to the antibody-chip. Finally, to detect Shiga toxins from Escherichia coli O157:H7, globotrisaccharide (Gb(3)) with an azido-triethylene glycol was synthesized and immobilized onto the SiN chip by the click reaction. The Gb(3)-SiN chips enabled us to detect the toxins at concentrations less than 100 ng/mL. RCA(120), horse gram, gorse lectins and BSA showed no response to the Gb(3)-SiN chip, showing a high specificity for the toxin.
• SATO, SUSUMU;NUNOMURA, SHIGEKI;NAKANO, TAKAHISA;ITO, YUKISHIGE;OGAWA, TOM+, TETRAHEDRON LETT., 29,(1988) N 33, C. 4097-4100
  作者：SATO, SUSUMU、NUNOMURA, SHIGEKI、NAKANO, TAKAHISA、ITO, YUKISHIGE、OGAWA, TOM+

  DOI：——

  日期：——