D-glycero-D-talo-heptonic acid 4-lactone | 15397-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: D-glycero-D-talo-heptonic acid 4-lactone
• 英文别名: D-glycero-D-talo-Heptonsaeure-4-lacton；γ-Lacton der d-Manno-β-heptonsaeure；D-manno-β-heptonic acid γ-lactone；d-Glycero-d-talo-heptono-1,4-lactone；(3S,4R,5S)-3,4-dihydroxy-5-[(1R,2R)-1,2,3-trihydroxypropyl]oxolan-2-one
• CAS: 15397-09-8
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: VIVCRCODGMFTFY-TVIMKVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  D-glycero-D-talo-heptonic acid 4-lactone 在 camphor-10-sulfonic acid 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 42.0h， 生成 2,3-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone
  参考文献：
  名称：

  Acetonides of heptonolactones: Powerful chirons

  摘要：

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.

  DOI：

  10.1016/s0957-4166(00)82201-6
• 作为产物：
  描述：

  D-mannose 在 硫酸 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 17.0h， 生成 D-glycero-D-talo-heptonic acid 4-lactone
  参考文献：
  名称：

  Acetonides of heptonolactones: Powerful chirons

  摘要：

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.

  DOI：

  10.1016/s0957-4166(00)82201-6

文献信息

• Synthesis of <scp>L</scp>-glucurone. Conversion of <scp>D</scp>-glucose into <scp>L</scp>-glucose
  作者：Walter Sowa

  DOI：10.1139/v69-655

  日期：1969.11.1

  L-Glucurone (2) was readily prepared on a small scale by treatment of D-glycero-D-gulo-heptono-lactone (1) with a molar equivalent of periodic acid; thin–layer chromatography was used for its isolation. On a larger scale pure crystalline L-glucurone was obtained in over 80% yield from 3,5;6,7-di-O-isopropylidene-D-glycero-D-gulo-heptonolactone (4) in two steps consisting of concomitant hydrolysis and oxidation of 4 with periodic acid followed by treatment of the intermediate oxidation product with trifluoroacetic acid. L-Glucose was prepared from L-glucurone by borohydride reduction and hydrolysis of the 1,2-O-isopropylidene derivative. Since 1 was derived from D-glucose, the result of this series of reactions was the conversion of D-glucose into its enantiomer L-glucose.

  L-葡萄糖醛酸（2）可通过将D-甘油-D-戈洛-庚酮内酯（1）与等摩尔的碘酸处理而在小规模下快速制备；薄层色谱法用于其分离。在较大规模上，通过将3,5;6,7-二-O-异丙基-D-甘油-D-戈洛-庚内酯（4）与碘酸同时水解和氧化的两步反应，然后用三氟乙酸处理中间氧化产物，可获得纯结晶L-葡萄糖醛酸，收率超过80%。L-葡萄糖可通过对L-葡萄糖醛酸进行硼氢化物还原和对1,2-O-异丙基内酯衍生物的水解而制备。由于1来源于D-葡萄糖，这一系列反应的结果是将D-葡萄糖转化为其对映异构体L-葡萄糖。
• Bicyclic tetrahydroxylated pyrrolizidines
  申请人：Monsanto Company

  公开号：US04992460A1

  公开（公告）日：1991-02-12

  Novel bicyclic tetrahydroxylated pyrrolizidines are disclosed which are inhibitors of glycosidase enzymes. A preferred inhibitor is 1.alpha., 2.alpha., 6.alpha., 7.alpha., 7.alpha..beta.-1,2,6,7-tetrahydroxypyrrolizidine. It is synthesized from D-glycero-D-gulo-heptono-1,4-lactone. Novel Intermediate compounds prepared during this synthesis are 7-O-tert-butyldiphenylsilyl-2,3:5,6-di-O-isopropylidene-D-glycero-D-gulo-h ept ono-1,4-lactone and 1.alpha., 2.alpha., 6.alpha., 7.alpha., 7.alpha..beta.-1,2:6,7-di-O-isopropylidene-1,2,6,7-tetrahydroxypyrrolizidi ne.

  本发明涉及一种新型的双环四羟基吡咯烷衍生物，其为糖苷酶酶抑制剂。其中一种优选的抑制剂为1α、2α、6α、7α、7α.β-1,2,6,7-四羟基吡咯烷。该化合物是由D-甘露醇-D-戊糖-1,4-内酯合成的。在该合成过程中，制备了一些新型的中间体化合物，包括7-O-叔丁基二苯基硅基-2,3:5,6-二-O-异丙基亚甲基-D-甘露醇-D-戊糖-1,4-内酯和1α、2α、6α、7α、7α.β-1,2:6,7-二-O-异丙基亚甲基-1,2,6,7-四羟基吡咯烷。
• Method of preparing bicyclic tetrahydroxylated pyrrolizidines
  申请人：Monsanto Company

  公开号：US05026870A1

  公开（公告）日：1991-06-25

  Novel bicyclic tetrahydroxylated pyrrolizidines are disclosed which are inhibitors of glycosidase enzymes. A preferred inhibitor is 1.alpha.,2.alpha.,6.alpha.,7.alpha.,7.alpha..beta.-1,2,6-7-tetrahydroxypyr rolizidine. It is synthesized from D-glycero-D-gulo-heptono-1,4-lactone.

  本发明揭示了一种新型的双环四羟基吡咯烷衍生物，可用作糖苷酶的抑制剂。其中一种优选的抑制剂为1.alpha.，2.alpha.，6.alpha.，7.alpha.，7.alpha..beta.-1,2,6-7-四羟基吡咯烷。该化合物可由D-甘露醇-D-戊糖酮-1,4-内酯合成。
• Peirce, Journal of Biological Chemistry, 1915, vol. 23, p. 337
  作者：Peirce

  DOI：——

  日期：——
• Isbell, Journal of Research of the National Bureau of Standards (United States), 1938, vol. 20, p. 97,105
  作者：Isbell

  DOI：——

  日期：——