ethyl 4-O-acetyl-2,6-di-O-benzoyl-3-O-chloroacetyl-1-thio-β-D-galactopyranoside | 404391-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-acetyl-2,6-di-O-benzoyl-3-O-chloroacetyl-1-thio-β-D-galactopyranoside
• 英文别名: Bz(-2)[ClAc(-3)][Bz(-6)]Gal4Ac(b)-SEt；[(2R,3S,4S,5R,6S)-3-acetyloxy-5-benzoyloxy-4-(2-chloroacetyl)oxy-6-ethylsulfanyloxan-2-yl]methyl benzoate
• CAS: 404391-05-5
• 化学式: C₂₆H₂₇ClO₉S
• 分子量: 551.014
• InChiKey: TVQFVAMSBBDYPR-UEENZAOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 4-O-acetyl-2,6-di-O-benzoyl-3-O-chloroacetyl-1-thio-β-D-galactopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 4-O-acetyl-2,6-di-O-benzoyl-3-O-chloroacetyl-β-D-galactopyranosyl bromide
  参考文献：
  名称：

  Synthesis of a spacer-armed disulfated tetrasaccharide of SB1a, a carbohydrate hapten associated with human hepatocellular carcinoma

  摘要：

  A disulfated tetrasaccharide fragment with a spacer arm of human hepatocellular carcinoma carbohydrate antigen SB1a, namely, 2-aminoethyl 3-O-sulfo-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-3-O-sulfo-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranoside was synthesized via a [2 + 1 + 1] block building mode. In the last coupling step toward the trisaccharide acceptor 8, benzoyl protected galactosyl bromide donor 14 was found to be much more reactive than the acetyl-protected donors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00291-4
• 作为产物：
  描述：

  氯乙酰氯 、 ethyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83.7%的产率得到ethyl 4-O-acetyl-2,6-di-O-benzoyl-3-O-chloroacetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a spacer-armed disulfated tetrasaccharide of SB1a, a carbohydrate hapten associated with human hepatocellular carcinoma

  摘要：

  A disulfated tetrasaccharide fragment with a spacer arm of human hepatocellular carcinoma carbohydrate antigen SB1a, namely, 2-aminoethyl 3-O-sulfo-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-3-O-sulfo-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranoside was synthesized via a [2 + 1 + 1] block building mode. In the last coupling step toward the trisaccharide acceptor 8, benzoyl protected galactosyl bromide donor 14 was found to be much more reactive than the acetyl-protected donors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00291-4

文献信息

• Bromonium ion-promoted glycosidic bond formation and simultaneous bromination of an activated aryl aglycon
  作者：Zhi-Hui Qin、Hui Li、Meng-Shen Cai、Zhong-Jun Li

  DOI：10.1016/s0008-6215(01)00276-2

  日期：2002.1

  N-Bromosuccinimide (NBS) together with a catalytic amount of Me3SiOTf was found to be effective for the activation of thioglycosides. Concurrently with formation of the glycosidic bond, bromination took place on the activated aromatic ring of a 4-methoxyphenyl aglycon. (C) 2002 Elsevier Science Ltd. All rights reserved.