2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose | 116182-08-2

• 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-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose
• 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-and-β-D-glucopyranosyl acetate；acetyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)(1->4)-2,3,6-tri-O-acetyl-D-glucopyranoside；D-Globotriose undecaacetate；[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3R,4S,5R)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 116182-08-2
• 化学式: C₄₀H₅₄O₂₇
• 分子量: 966.853
• InChiKey: NNLVGZFZQQXQNW-ZPJDOXTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.29
• 重原子数：
  67.0
• 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：
  335.45
• 氢给体数：
  0.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose 在 碘代三甲硅烷 、 2,6-二叔丁基-4-甲基苯酚 、 碘 作用下， 以 氯仿 为溶剂， 20.0~70.0 ℃ 、275.8 kPa 条件下， 反应 1.16h， 生成 3-iodopropyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-acetyl-β-O-D-galactopyranosyl)-(1→4)-O-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  使用糖基碘和三亚甲基氧对寡糖进行两步官能化及其在多价糖缀合物中的应用

  摘要：

  寡糖结合物，如糖蛋白和糖脂，是潜在的化学治疗剂，也是了解碳水化合物生物学作用的有用工具。随着许多现代分离和合成技术提供了对各种游离糖的访问，对碳水化合物功能化的通用方法的需求日益增加。在此，我们提出一个两步方法论的结合per- Ø -acetylated寡糖功能化的接头，可用于各种显示器。从合成和商业来源获得的寡糖被转化为糖基碘并用 I 2活化形成反应性供体，随后用三亚甲基氧捕获，一步形成碘丙基结合物。末端碘化物作为进一步修饰的化学柄。转化为相应的叠氮化物，然后进行铜催化的叠氮化物-炔烃环加成反应，提供了 Gb3 的多价糖缀合物，用于进一步研究作为抗癌疗法。

  DOI：

  10.1002/chem.201400024
• 作为产物：
  描述：

  (2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-2-hydroxymethyl-tetrahydro-pyran-3-ol 、 乙酸酐 在 palladium on activated charcoal 氢气 、 吡啶 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以89%的产率得到2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents

  摘要：

  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.

  DOI：

  10.1016/j.carres.2006.03.044

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：——