4,5,7,8-tetra-O-benzyl-3-deoxy-1-(propane-1,3-diyl-dithioacetal)-α-D-manno-octopyranosyl-(2->6)-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside) | 320343-73-5

• 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->6)-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside)
• 英文别名: (2R,3R,4S,5R,6S)-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]oxymethyl]-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 320343-73-5
• 化学式: C₆₇H₇₄O₁₁S₂
• 分子量: 1119.45
• InChiKey: KOKVRRBYSRTFAO-SJDFVBPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  80
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  13

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->6)-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside) 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 水 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 为溶剂， 生成 (2R,4R,5R,6R)-6-((R)-1,2-Dihydroxy-ethyl)-4,5-dihydroxy-2-((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  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：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 (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76%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->6)-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside)
  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.