(2R,3R,5S,6R,7R)-5,6,7,8-Tetrahydroxy-1,2,3-trimethoxy-octan-4-one | 186378-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,5S,6R,7R)-5,6,7,8-Tetrahydroxy-1,2,3-trimethoxy-octan-4-one
• 英文别名: (2R,3R,5S,6R,7R)-5,6,7,8-tetrahydroxy-1,2,3-trimethoxyoctan-4-one
• CAS: 186378-62-1
• 化学式: C₁₁H₂₂O₈
• 分子量: 282.291
• InChiKey: DYARQLPIVGQPGS-LPZLMQDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,5S,6R,7R)-5,6,7,8-Tetrahydroxy-1,2,3-trimethoxy-octan-4-one 在 sodium periodate 作用下， 以 甲醇 为溶剂， 反应 24.5h， 生成 methyl 2,3,4-tri-O-methyl-(+)-D-erythronate
  参考文献：
  名称：

  A highly diastereoselective synthesis of 4-octulose and 2-deoxy-4-octulose from a d-fructose derivative

  摘要：

  Bishydroxylation of methyl (Z)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-beta-D-arabino-oct-2-ene-4-ulo-4,8-pyranosonate 1 with osmium tetraoxide proceeded with extremed high diastereoselectivity to give only methyl 4,5:6,7-di-O-isopropylidene-beta-D-arabino-L-erythro-oct-4-ulo-4,8-pyranosonate 2. Configurations of the new stereogenic centers (C-2,3) in 2 were determined by degradation of the C-5,6,7,8 fragment to the well-known methyl 2,3,4-tri-O-methyl-D-(+)-erythronate. 7. Transformation of 2 into the required D-arabino-L-erythro-oct-4-ulosa 10, was achieved by a methodology that implied, protection to 8, reduction of the ester group in 8 to a hydroxymethyl group in 9, and finally deprotection to the free D-arabino-L-erythro-oct-4-ulosa 10. On the other hand, epoxidation reaction on (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-beta-D-arabino-oct-2-ene-4-ulo-4,8-pyranose 11 afforded only the corresponding 2,3-anhydro derivative 12 with beta-D-arabino-D-threo configuration, as could be demonstrated by degradation to (S)-1,2,4-trimetoxybutane 16, which synthesis is reported herein. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00468-5
• 作为产物：
  描述：

  (2S,3R)-2,3-Dimethoxy-3-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-propionic acid methyl ester 在 咪唑 、 lithium aluminium tetrahydride 、 sodium hydride 、 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 49.5h， 生成 (2R,3R,5S,6R,7R)-5,6,7,8-Tetrahydroxy-1,2,3-trimethoxy-octan-4-one
  参考文献：
  名称：

  A highly diastereoselective synthesis of 4-octulose and 2-deoxy-4-octulose from a d-fructose derivative

  摘要：

  Bishydroxylation of methyl (Z)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-beta-D-arabino-oct-2-ene-4-ulo-4,8-pyranosonate 1 with osmium tetraoxide proceeded with extremed high diastereoselectivity to give only methyl 4,5:6,7-di-O-isopropylidene-beta-D-arabino-L-erythro-oct-4-ulo-4,8-pyranosonate 2. Configurations of the new stereogenic centers (C-2,3) in 2 were determined by degradation of the C-5,6,7,8 fragment to the well-known methyl 2,3,4-tri-O-methyl-D-(+)-erythronate. 7. Transformation of 2 into the required D-arabino-L-erythro-oct-4-ulosa 10, was achieved by a methodology that implied, protection to 8, reduction of the ester group in 8 to a hydroxymethyl group in 9, and finally deprotection to the free D-arabino-L-erythro-oct-4-ulosa 10. On the other hand, epoxidation reaction on (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-beta-D-arabino-oct-2-ene-4-ulo-4,8-pyranose 11 afforded only the corresponding 2,3-anhydro derivative 12 with beta-D-arabino-D-threo configuration, as could be demonstrated by degradation to (S)-1,2,4-trimetoxybutane 16, which synthesis is reported herein. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00468-5