[(3aS,4R,6R,7R,7aS)-7-benzoyloxy-6-bromo-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate | 155679-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3aS,4R,6R,7R,7aS)-7-benzoyloxy-6-bromo-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
• CAS: 155679-30-4
• 化学式: C₂₃H₂₃BrO₇
• 分子量: 491.335
• InChiKey: JOPPLXCDXRFDJR-CXQPBAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(3aS,4R,6R,7R,7aS)-7-benzoyloxy-6-bromo-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 0.33h， 生成 4-pentenyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of cancer-associated glycoantigens: stage-specific embryonic antigen 3 (SSEA-3)

  摘要：

  The synthesis of the tumor-associated carbohydrate antigens SSEA-3 and Gb3 in a semi-convergent fashion using building blocks bearing a S-thiazolinyl (STaz) moiety is reported. Complete stereoselective control of a difficult alpha-(1 -> 4)-galactosylation and high overall yields were achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.041
• 作为产物：
  描述：

  乙基-2,6-二-氧-苯甲酰基-3,4-氧-异丙叉-Β-D-硫代吡喃半乳糖苷 在 3 A molecular sieve 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 [(3aS,4R,6R,7R,7aS)-7-benzoyloxy-6-bromo-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
  参考文献：
  名称：

  Synthesis of cancer-associated glycoantigens: stage-specific embryonic antigen 3 (SSEA-3)

  摘要：

  The synthesis of the tumor-associated carbohydrate antigens SSEA-3 and Gb3 in a semi-convergent fashion using building blocks bearing a S-thiazolinyl (STaz) moiety is reported. Complete stereoselective control of a difficult alpha-(1 -> 4)-galactosylation and high overall yields were achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.041

文献信息

• Disaccharide derivatives and processes for the preparation thereof
  申请人：The Nisshin Oil Mills, Ltd.

  公开号：EP0578112A2

  公开（公告）日：1994-01-12

  Disaccharide derivatives selected from the group consisting of the compounds represented by formulas (I) and (II) in which R₁ represents C₁-C₄ alkyl or phenyl, R₂ represents benzyl or methoxybenzyl, Bn stands for benzyl, Bz stands for benzoyl, MPM stands for methoxybensyl, Me stands for methyl and NPhth stands for phthalimide of the formula Those derivatives can be used as intermediates for the preparation of sialyl SSEA-1 ganglioside and other lacto-and neolacto-series gangliosides which are useful as tumor markers in a serum diagnosis of cancers.

  从由式（I）和（II）表示的化合物组中选择的二糖衍生物，其中R₁表示C₁-C₄烷基或苯基，R₂表示苄基或甲氧基苄基，Bn代表苄基，Bz代表苯甲酰基，MPM代表甲氧基苄基，Me代表甲基，NPhth代表邻苯二甲酰亚胺的公式。这些衍生物可用作神经节苷脂sialyl SSEA-1和其他乳糖和新乳糖系列神经节苷脂的中间体，在血清癌症诊断中作为肿瘤标记物有用。
• Synthesis of cancer-associated glycoantigens: stage-specific embryonic antigen 3 (SSEA-3)
  作者：Papapida Pornsuriyasak、Alexei V. Demchenko

  DOI：10.1016/j.carres.2006.03.041

  日期：2006.7

  The synthesis of the tumor-associated carbohydrate antigens SSEA-3 and Gb3 in a semi-convergent fashion using building blocks bearing a S-thiazolinyl (STaz) moiety is reported. Complete stereoselective control of a difficult alpha-(1 -> 4)-galactosylation and high overall yields were achieved. (c) 2006 Elsevier Ltd. All rights reserved.