(3aS,4R,6R,7S,7aR)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol | 174782-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,6R,7S,7aR)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol
• CAS: 174782-39-9
• 化学式: C₁₄H₂₅NO₅
• 分子量: 287.356
• InChiKey: ZSAAVIMIAHFMDQ-HRRXFJGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.18
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6R,7S,7aR)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol 在 Dowex 50W-X₈ 、 四丁基碘化铵 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 17.0h， 生成 (3aS,4R,6S,7S,7aR)-7-Benzyloxy-6-((S)-1,2-dihydroxy-ethyl)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  Aza-C-disaccharides:  Synthesis of 6-Deoxygalactonojirimycin β-C(1→3) Linked with d-Altrofuranosides and d-Galactose

  摘要：

  Cross-aldolization of 3-O-benzyl-N-(benzyloxycarbonyl)-2,6,7-trideoxy-2,6-imino-4,5-O-isopropylidene-beta-D-glycero-L-mannoheptose ((-)- 12, derived from D-glycero-D-gulo-heptono-1,4-lactone in eight steps with (+)-(1R,4S,5S,6S)- and (-)-(1S,4R,5R,6R)-6-chloro-5-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one (obtained in one step from the ''naked sugars'' (-)- and (+)-7-oxabicyclo[2,2.1]hept-5-en-2-one) were highly stereoselective (lithium enolates, like modes, giving aldols (-)- 14 and (+)- 16, respectively. Stereoselective methods were developed for the conversion of(-)- 14 into methyl -imino-beta-D-glycero-L-manno-heptitol-1'-yl]-alpha and -beta-D-altro-furanoside ((+)-1 alpha,beta). The aza-C-disaccharide 1 alpha prefers a anti conformation (bonds C(2')-C(3') and C(1')-C(3) are antiperiplanar) for the beta-D-galactoside moiety ((3)J(H,H) coupling constants, NOEs). Aldol(+)- 16 was converted stereoselectively into 3-deoxy-3-C-[(1'S)-2',6',7'-trideoxy -2 D-glycero-L-manno-heptitol-1'-yl]-beta-D-galactose trifluoroacetate.

  DOI：

  10.1021/jo970151t
• 作为产物：
  描述：

  (3aR,6S,6aR)-6-[(R)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (3aS,4R,6R,7S,7aR)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,4-trimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol
  参考文献：
  名称：

  D-altrose衍生物的β-D-（1→3）-C键合的1,5,6-三苯氧基-1,5-亚氨基半乳糖苷的合成

  摘要：

  标题氮杂-C-二糖是通过2,6,7-三苯氧基-2,6-亚氨基-D-甘油-L-甘露糖和7-氧杂草烷酮衍生物的高度立体选择性交叉醛缩醛化获得的。

  DOI：

  10.1016/0040-4039(95)02214-7

文献信息

• Synthesis of (+)-3,7,8-trideoxy-3,7-imino-d-threo-l-galacto-octitol and its inhibition of β-glucosidases
  作者：Alain Baudat、Sylviane Picasso、Pierre Vogel

  DOI：10.1016/0008-6215(95)00348-7

  日期：1996.2

  The readily available 2,3:6,7-di-O-isopropylidene-D-glycero-D-gulo-heptono-1,4-lactone [(-)-5] was converted in four synthetic steps into the new iminooctitol (+)-3,7,8-trideoxy-3,7-imino-D-threo-L-galacto-octitol [(+)-10]. Although the piperidine unit of (+)-10 has the absolute configuration of beta-D-galacto-hexopyranosides, this iminoalditol does not inhibit five commercially available beta-galactosidases

  易于获得的2,3：6,7-二-O-异亚丙基-D-甘油-D-古洛庚酮-1,4-内酯[（-）-5]通过四个合成步骤转化为新的亚氨基辛醇（ +）-3,7,8-三甲氧基-3,7-亚氨基-D-苏-L-半乳糖辛醇[（+）-10]。尽管（+）-10的哌啶单元具有β-D-半乳糖-己吡喃糖苷的绝对构型，但该亚氨基糖醇不会抑制5种市售的β-半乳糖苷酶。但是，发现（+）-10是来自杏仁（Ki = 15μM）和来自解糖Caldocellum saccharolyticum（Ki = 41μM）的β-葡萄糖苷酶的良好竞争性抑制剂。