| 177421-46-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• CAS: 177421-46-4
• 化学式: C₁₅H₂₂O₇
• 分子量: 314.335
• InChiKey: DALHDLCBPUVMIP-XBHUSJMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 四氧化锇 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 copper(II) sulfate 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 242.5h， 生成 (2R,3R,5S,6R,7R)-1,2,3,5,6,7,8-Heptahydroxy-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
• 作为产物：
  描述：

  果糖二丙酮 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of 4-Octuloses from a Derivative ofd-Fructose

  摘要：

  Reaction of 2,3:4,5-di-O-isopropylidene-beta-D-arabino-hexos-2-ulo-2,6-pyranose (1) with (methoxycarbonylmethylene)triphenylphosphorane in either dichloromethane or methanol gave methyl (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-beta-D-arabino-oct-2-ene-4-ulo-4,8-pyranosonate (2) or a 1:2.3 mixture of 2 and its Z-isomer (3), respectively. Bishydroxylation of 2 with osmium tetraoxide gave a mixture of methyl 4,5:6,7-di-O-isopropylidene-beta-D-glycero-D-galacto- (4) and -D-glycero-D-ido-oct-4-ulo-4,8-pyranosonate (5) which were carefully resolved by column chromatography. Compound 4 was transformed into its 2,3-di-O-methyl derivative (6) which was deacetonated to 7 and subsequently degraded to dimethyl 2,3-di-O-methyl-(+/-)-L-tartrate (8). On the other hand, acetonation of a mixture of 4 and 5 gave the corresponding tri-O-isopropylidene derivatives (9) and (10). Compounds 4 and 5 were reduced with LiAlH4 to the related 4,5:6,7-di-O-isopropylidene-beta-D-glycero-D-galacto- (11) and -beta-D-glycero-D-ido-oct-4-ulo-4,8-pyranose (12). Treatment of 11 and 12 with acetone/PTSA/CuSO4 only produced the acetonation at the C-2,3 positions. Finally, compounds 11 and 12 were deacetonated to the corresponding D-glycero-D-galacto- (15) and D-glycero-D-ido-oct-4-ulose (16).

  DOI：

  10.1080/07328309608005655