4,5,7,8-tetra-O-benzyl-3-deoxy-1-(propane-1,3-diyl-dithioacetal)-α-D-manno-octopyranosyl-(2->7)-(methyl 2,3,4,6-tetra-O-benzyl-α-D-manno-heptopyranoside) | 320343-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5,7,8-tetra-O-benzyl-3-deoxy-1-(propane-1,3-diyl-dithioacetal)-α-D-manno-octopyranosyl-(2->7)-(methyl 2,3,4,6-tetra-O-benzyl-α-D-manno-heptopyranoside)
• 英文别名: (2R,3S,4S,5S,6S)-2-[(1S)-2-[(2R,4R,5R,6R)-6-[(1R)-1,2-bis(phenylmethoxy)ethyl]-2-(1,3-dithian-2-yl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-1-phenylmethoxyethyl]-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 320343-75-7
• 化学式: C₇₅H₈₂O₁₂S₂
• 分子量: 1239.6
• InChiKey: YPQMUPRNLFKXON-ZQAKEWQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  89
• 可旋转键数：
  32
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4,5,7,8-tetra-O-benzyl-3-deoxy-1-(propane-1,3-diyl-dithioacetal)-α-D-manno-octopyranosyl-(2->7)-(methyl 2,3,4,6-tetra-O-benzyl-α-D-manno-heptopyranoside) 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,4R,5R,6R)-4,5-Bis-benzyloxy-2-[(S)-2-benzyloxy-2-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-6-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthetic approach to 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) α-disaccharides via a ketene dithioacetal

  摘要：

  A unique strategy for the synthesis of Kdo cc-disaccharides based on the ketene dithioacetal 4 (precursor of Kdo) as a 'glycosyl donor' has been developed. Direct, fully stereoselective addition of 6-, 7-, or 8-OH unprotected sugar units to the exo-anomeric double bond in 4, promoted by trimethylsilyl triflate, led to the corresponding O-disaccharides 12 with the dithioacetal residue intact. Subsequent hydrolysis of the later afforded the title compounds in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00371-2
• 作为产物：
  描述：

  methyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside 、 (2R,3R,4R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-6-(1,3-dithian-2-ylidene)-3,4-bis(phenylmethoxy)oxane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到4,5,7,8-tetra-O-benzyl-3-deoxy-1-(propane-1,3-diyl-dithioacetal)-α-D-manno-octopyranosyl-(2->7)-(methyl 2,3,4,6-tetra-O-benzyl-α-D-manno-heptopyranoside)
  参考文献：
  名称：

  Synthetic approach to 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) α-disaccharides via a ketene dithioacetal

  摘要：

  A unique strategy for the synthesis of Kdo cc-disaccharides based on the ketene dithioacetal 4 (precursor of Kdo) as a 'glycosyl donor' has been developed. Direct, fully stereoselective addition of 6-, 7-, or 8-OH unprotected sugar units to the exo-anomeric double bond in 4, promoted by trimethylsilyl triflate, led to the corresponding O-disaccharides 12 with the dithioacetal residue intact. Subsequent hydrolysis of the later afforded the title compounds in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00371-2

文献信息

• Synthetic approach to 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) α-disaccharides via a ketene dithioacetal
  作者：Jacek Młynarski、Anna Banaszek

  DOI：10.1016/s0957-4166(00)00371-2

  日期：2000.9

  A unique strategy for the synthesis of Kdo cc-disaccharides based on the ketene dithioacetal 4 (precursor of Kdo) as a 'glycosyl donor' has been developed. Direct, fully stereoselective addition of 6-, 7-, or 8-OH unprotected sugar units to the exo-anomeric double bond in 4, promoted by trimethylsilyl triflate, led to the corresponding O-disaccharides 12 with the dithioacetal residue intact. Subsequent hydrolysis of the later afforded the title compounds in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.