O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-methanesulfonyl-α-D-allofuranose | 22331-20-0

• 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: O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-methanesulfonyl-α-D-allofuranose
• 英文别名: [(2R)-2-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methylsulfonyloxyethyl] methanesulfonate
• CAS: 22331-20-0
• 化学式: C₁₈H₂₆O₁₀S₂
• 分子量: 466.53
• InChiKey: IDNRCCMUOSKKJV-WRQOLXDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-methanesulfonyl-α-D-allofuranose 在 盐酸 、 sodium iodide 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 16.0h， 生成 (2R,3R,4S,5R)-4-Benzyloxy-5-vinyl-tetrahydro-furan-2,3-diol
  参考文献：
  名称：

  Studies on the Synthesis of the C-Glycosidic Part of Nogalamycin, Part 2

  摘要：

  The stereochemistry of the addition of metalloaryls 11w-z to the methyl ketones 10a-e was studied in connection with the construction of the hogalamycin C-glycoside. Excellent selectivities towards the (S)-isomer 13a were observed in the beta-chelate model B in the reaction of the benzyl ethers 10a with the cerium reagent 11y and the titanium reagent 11z or the alcohol 10c with the lithium compound 11w. A moderate 3:1 selectivity in favor of the desired (R)-isomer was observed in the reaction of the silyl ether 10d with 11w. A reversal of the addition sequence (reaction of 15a with MeMgI) led exclusively to 13a whereas the alcohol 15c gave a 5:3 mixture of 12c:13c.

  DOI：

  10.1080/07328309808002321

文献信息

• Paulsen,H.; Stoye,D., Chemische Berichte, 1969, vol. 102, # 3, p. 820 - 833
  作者：Paulsen,H.、Stoye,D.

  DOI：——

  日期：——
• US5338865A
  申请人：——

  公开号：US5338865A

  公开（公告）日：1994-08-16
• US5436238A
  申请人：——

  公开号：US5436238A

  公开（公告）日：1995-07-25
• Studies on the Synthesis of the <i>C</i>-Glycosidic Part of Nogalamycin, Part 2
  作者：Karsten Krohn、Ulrich Flörke、Jürgen Keine、Ina Terstiege

  DOI：10.1080/07328309808002321

  日期：1998.3.1

  The stereochemistry of the addition of metalloaryls 11w-z to the methyl ketones 10a-e was studied in connection with the construction of the hogalamycin C-glycoside. Excellent selectivities towards the (S)-isomer 13a were observed in the beta-chelate model B in the reaction of the benzyl ethers 10a with the cerium reagent 11y and the titanium reagent 11z or the alcohol 10c with the lithium compound 11w. A moderate 3:1 selectivity in favor of the desired (R)-isomer was observed in the reaction of the silyl ether 10d with 11w. A reversal of the addition sequence (reaction of 15a with MeMgI) led exclusively to 13a whereas the alcohol 15c gave a 5:3 mixture of 12c:13c.