3,4:6,7-di-O-isopropylidene-L-glycero-D-galacto-heptono-1,5-lactone | 137126-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4:6,7-di-O-isopropylidene-L-glycero-D-galacto-heptono-1,5-lactone
• 英文别名: (3aR,4R,7R,7aR)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-7-hydroxy-2,2-dimethyltetrahydro-[1,3]-dioxolo-[4,5-c]-pyran-6-one；Hqvjtktxelkpid-chhowfrjsa-；(3aR,4R,7R,7aR)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 137126-25-1
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: HQVJTKTXELKPID-CHHOWFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4:6,7-di-O-isopropylidene-L-glycero-D-galacto-heptono-1,5-lactone 在 吡啶 、 叠氮阴离子 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,4R,7S,7aR)-7-azido-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]-dioxolo-[4,5-c]-pyran-6-one
  参考文献：
  名称：

  Alexines from heptonolactones

  摘要：

  Syntheses of 1,7a-diepialexine and 1,7,7a-triepialexine from heptonolactones are reported.

  DOI：

  10.1016/0040-4039(91)80072-e
• 作为产物：
  描述：

  6-(2,2-二甲基-[1,3]二氧杂烷-4-基) -2,2-二甲基-二氢-呋喃并[3,4-d][1 ,3]二氧代-4-酮 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正庚烷 、 水 为溶剂， 反应 4.5h， 生成 3,4:6,7-di-O-isopropylidene-L-glycero-D-galacto-heptono-1,5-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

• [EN] GLYCOSIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE GLYCOSIDASES ET LEURS UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2014032184A1

  公开（公告）日：2014-03-06

  The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.

  该发明提供了用于抑制糖苷酶的化合物，这些化合物的前药，以及包括这些化合物或这些化合物的前药的药物组合物。该发明还提供了用于治疗与O-GlcNAcase缺乏或过度表达、O-GlcNAc的积累或缺乏相关的疾病和障碍的方法。
• GLYCOSIDASE INHIBITORS AND USES THEREOF
  申请人：Alectos Therapeutics Inc.

  公开号：US20150299122A1

  公开（公告）日：2015-10-22

  The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.

  本发明提供了抑制糖苷酶的化合物，该化合物的前药，以及包括该化合物或该化合物的前药的制药组合物。本发明还提供了治疗与O-GlcNA酶的缺乏或过度表达、O-GlcNAc的积累或缺乏有关的疾病和障碍的方法。
• Method for azide displacement of alpha-triflates of 1,5-lactones
  申请人：MONSANTO COMPANY

  公开号：EP0398857A3

  公开（公告）日：1991-05-08

  Reactions of azide ion with 2-O-trifluoro-methanesulphonates of both 3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone (1) and of 3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-1,5-lactone (2) are disclosed to give predominantly 2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-1,5-lactone (4) initially which then isomerizes under moderate reaction conditions to 2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone (3).

  本研究公开了叠氮离子与 3,4:6,7-二-O-异亚丙基-D-甘油-D-半乳-庚-1,5-内酯 (1) 和 3,4:6,7-二-O-异亚丙基-D-甘油-D-半乳-庚-1,5-内酯 (2) 的 2-O-三氟甲磺酸盐的反应，主要得到 2-叠氮-2-脱氧-3,4,6,7-二-O-异亚丙基-D-甘油-D-半乳-庚-1,5-内酯 (4)：6,7- 二-O-异亚丙基-D-甘油-D-半乳-庚-1,5-内酯（4），然后在中等反应条件下异构化为 2-叠氮-2-脱氧-3,4:6,7-二-O-异亚丙基-D-甘油-D-半乳-庚-1,5-内酯（3）。
• Bicyclic tetrahydroxypyrrolizidine
  申请人：MONSANTO COMPANY

  公开号：EP0417060A2

  公开（公告）日：1991-03-13

  Novel bicyclic tetrahydroxylated pyrrolizidines are disclosed which are inhibitors of glycosidase enzymes. A preferred inhibitor is (1S,2R,6R,7S)-1,2,6-­7-tetrahydroxypyrrolizidine. It is synthesized from D-­glycero-talo-heptono-1,4-lactone.

  本研究公开了新型双环四羟基吡咯烷类化合物，它们是糖苷酶的抑制剂。一种优选的抑制剂是 (1S,2R,6R,7S)-1,2,6-7-四羟基吡咯烷。它是由 D-甘油-卤代-庚-1,4-内酯合成的。
• Synthesis of mannojirimycin derivatives
  申请人：MONSANTO COMPANY

  公开号：EP0427694A1

  公开（公告）日：1991-05-15

  α-Homomannojirimycin (1) and 6-epi-homomannojirimycin (2) are each synthesized from 2-azido-2-deoxy-3,4:6,7-di-O-­isopropylidene-D-glycero-D-talo-heptono-1,5-lactone (3) in which the side chain acetonide is hydrolyzed to give the corresponding diol which is then protected with a silyl protecting agent to form a silyl ether. The latter compound is used as a divergent intermediate in which the piperidine ring is formed by joining the nitrogen function at C-2 to C-6 (A) with inversion of configuration at C-6 to form 6-­epi-homomannojirimycin or (B) with retention of configuration at C-6 to form α-homomannojirimycin.

  α-高甘露尻霉素（1）和 6-表高甘露尻霉素（2）分别由 2-叠氮-2-脱氧-3,4:6,7-二-O-异亚丙基-D-甘油-D-卤代-庚-1,5-内酯（3）合成，其中侧链丙酮水解后得到相应的二元醇，然后用硅烷保护剂保护形成硅烷醚。后一种化合物可用作发散中间体，其中的哌啶环是通过将 C-2 位的氮功能连接到 C-6 位形成的（A），C-6 位的构型发生反转，形成 6-epi-homannojirimycin；或（B）C-6 位的构型保持不变，形成 α-homannojirimycin。