p-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 578007-60-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-6)]Gal(b1-4)[Bz(-2)][Bz(-3)][Bz(-6)]Glc(b)-O-Ph(4-OMe)；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-6-[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-(4-methoxyphenoxy)oxan-3-yl]oxy-3-hydroxyoxan-2-yl]methyl benzoate
• CAS: 578007-60-0
• 化学式: C₆₁H₅₂O₁₈
• 分子量: 1073.07
• InChiKey: DGGWTEWWARLDQR-YGVWDLIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  79
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  224
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 吡啶 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

  摘要：

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10365-3
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 水 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 p-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

  摘要：

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10365-3

文献信息

• Unusual α-glycosylation with galactosyl donors with a C2 ester capable of neighboring group participation
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1016/s0040-4039(03)00673-7

  日期：2003.4

  6-O-benzylidene-1-thio-β-d-galactopyranoside (15) as the donor, glycosylation of 2 gave α-linked products only, indicating that 4,6-O-benzylidenation led to α-stereoselectivity in spite of the C2 ester capable of neighboring group participation. Using 15 as the donor, glycosylation of mannose derivatives with 2- or 3-OH's, glucose with 2- or 3-OH's, galactose with 2-, or 3-, or 4-OH's, glucosamine and glucuronic

  4-甲氧基苯基2,3,6-三-O-苯甲酰基-β-d-吡喃葡萄糖苷（2）与异丙基3 - O-烯丙基-2,4,6-三-O-苯甲酰基-（9）或6的糖基化- ø -烯丙基-2,3,4-三ö苯甲酰基-1-硫代β-d吡喃半乳糖苷（7）作为供体，得到的α-和β连接混合物，而用异丙3- ö -氯乙酰基-2- ø -苯甲酰基-4,6- ö -benzylidene-（13）和异丙基3- ö -烯丙基-2- ø -苯甲酰基-4,6- ø -亚苄基-1-硫代-β-β-d吡喃半乳糖苷（15）作为供体，2的糖基化仅产生α-连接的产物，表明尽管C2酯能够相邻基团参与，但4,6- O-亚苄基化仍导致α-立体选择性。使用15作为供体，甘露糖衍生物与2-或3-OH's进行糖基化，葡萄糖与2-或3-OH's进行葡萄糖基化，半乳糖与2-或3-或4-或4-OH's进行半乳糖苷，葡糖胺和葡萄糖醛酸与4-OH进行糖基化。 ，以及带有
• Target-selective photo-degradation of verotoxin-1 and reduction of its cytotoxicity to Vero cells using porphyrin–globotriose hybrids
  作者：Atsushi Okochi、Shuho Tanimoto、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c3cc42957a

  日期：——

  Designed and synthesized porphyrin–globotriose hybrids effectively degraded verotoxin-1, which causes severe bloody diarrhoea and fetal hemolytic uremic syndrome (HUS). Degradation was achieved using long-wavelength UV or visible light irradiation in the absence of any additives and under neutral conditions. Moreover, the hybrids neutralized the cytotoxicity of verotoxin upon photo-irradiation.

  设计并合成的卟啉-三葡萄糖类杂化物有效降解了导致严重血性腹泻和胎儿溶血性尿毒症综合征（HUS）的毒素-1。降解是在中性条件下，使用长波长紫外线或可见光照射，并且不添加任何添加剂。此外，这些杂化物在光照射下中和了毒素的细胞毒性。
• A concise and practical synthesis of antigenic globotriose, α-d-Gal-(1→4)-β-d-Gal-(1→4)-β-d-Glc
  作者：Langqiu Chen、Xing-E. Zhao、Duan Lai、Zhiwei Song、Fanzuo Kong

  DOI：10.1016/j.carres.2006.03.029

  日期：2006.7

  A concise and practical synthesis of the antigenic globotriose, alpha-D-Gal-(1 -> 4)-beta-D-Gal-(1 -> 4)-beta-D-Glc (13), was achieved by coupling of a monosaccharide donor, 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (4) with a disaccharide acceptor, p-methoxyphenyl 2,3,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (8), followed by deprotection. In spite of the existence of a C-2-ester substituent capable of neighboring-group participation in the donor, the coupling gave exclusively the alpha-linkage in satisfactory yield. The acceptor 8 was readily obtained from selective 3-O-benzoylation of the galactosyl. ring of p-methoxyphenyl 2,6-di-O-benzoyl-beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (7), which was prepared from p-methoxyphenyl beta-D-lactoside (5) via isopropylidenation, benzoylation, and deisopropylidenation. Donor 4 was obtained from p-methoxylphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside (1) via selective 4,6-di-O-debenzoylation, oxidative removal of 1-O-MP, benzylidenation, and trichloroacetimidate formation. (c) 2006 Elsevier Ltd. All rights reserved.
• “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide
  作者：Shun-ichi Hashimoto、Hiroki Sakamoto、Takeshi Honda、Hiroshi Abe、Sei-ichi Nakamura、Shiro Ikegami

  DOI：10.1016/s0040-4039(97)10365-3

  日期：1997.12

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.