Acetic acid (2R,3R,4R,5R,6R)-4-((3aS,4R,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-acetoxymethyl-5-azido-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester | 218291-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,5R,6R)-4-((3aS,4R,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-acetoxymethyl-5-azido-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
• CAS: 218291-62-4
• 化学式: C₂₃H₂₇Cl₃N₄O₁₅
• 分子量: 705.844
• InChiKey: WTONTNGTFIJOAK-YAIWXPEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  250.26
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6R)-4-((3aS,4R,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-acetoxymethyl-5-azido-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 在 palladium on activated charcoal 2,3,5-三甲基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Synthetic and Immunological Studies on Clustered Modes of Mucin-Related Tn and TF O-Linked Antigens:  The Preparation of a Glycopeptide-Based Vaccine for Clinical Trials against Prostate Cancer

  摘要：

  The syntheses of two tumor-associated carbohydrate antigens, Tn and TF, have been achieved using glycal assembly and cassette methodologies. These synthetic antigens were subsequently clustered (c) and immunoconjugated to a carrier protein (KLH or BSA) or a synthetic lipopeptide (pam) for immunological study. Three Tn conjugates were used to vaccinate groups of mice, and all preparations proved to be immunogenic. The Tn(c) covalently linked to KLH (27-KLH) plus the adjuvant QS-21 was the optimal vaccine, inducing high median IgM and IgG titers against Tn(c) by ELISA. These antibodies were strongly reactive with the Tn(c) positive human colon cancer cell line LS-C but not the Tn(c) negative colon cancer cell Line LS-B by FAGS. The antibodies' reactivities with natural antigens were inhibited with synthetic Tn(c) but not with structurally unrelated compounds. On the basis of these results, vaccines containing 27-KLH and 30-pam plus QS-21 are being tested in patients with prostate cancer.

  DOI：

  10.1021/ja9825128
• 作为产物：
  描述：

  三氯乙腈 、 Acetic acid (3aS,4R,6R,7R,7aS)-6-((2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-hydroxy-tetrahydro-pyran-4-yloxy)-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以22%的产率得到Acetic acid (2R,3R,4R,5R,6R)-4-((3aS,4R,6R,7R,7aS)-7-acetoxy-4-acetoxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-acetoxymethyl-5-azido-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthetic and Immunological Studies on Clustered Modes of Mucin-Related Tn and TF O-Linked Antigens:  The Preparation of a Glycopeptide-Based Vaccine for Clinical Trials against Prostate Cancer

  摘要：

  The syntheses of two tumor-associated carbohydrate antigens, Tn and TF, have been achieved using glycal assembly and cassette methodologies. These synthetic antigens were subsequently clustered (c) and immunoconjugated to a carrier protein (KLH or BSA) or a synthetic lipopeptide (pam) for immunological study. Three Tn conjugates were used to vaccinate groups of mice, and all preparations proved to be immunogenic. The Tn(c) covalently linked to KLH (27-KLH) plus the adjuvant QS-21 was the optimal vaccine, inducing high median IgM and IgG titers against Tn(c) by ELISA. These antibodies were strongly reactive with the Tn(c) positive human colon cancer cell line LS-C but not the Tn(c) negative colon cancer cell Line LS-B by FAGS. The antibodies' reactivities with natural antigens were inhibited with synthetic Tn(c) but not with structurally unrelated compounds. On the basis of these results, vaccines containing 27-KLH and 30-pam plus QS-21 are being tested in patients with prostate cancer.

  DOI：

  10.1021/ja9825128