3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-galacto-hept-1-enitol | 162239-08-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-galacto-hept-1-enitol
• 英文别名: (2R,3S,4R,5S)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol；(2R,3S,4R,5S)-1,3,4,5-tetrakis(phenylmethoxy)hept-6-en-2-ol
• CAS: 162239-08-9
• 化学式: C₃₅H₃₈O₅
• 分子量: 538.684
• InChiKey: SQQYKEFUMBMTTK-HDBFZYDSSA-N

物化性质

• 沸点：
  664.2±55.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-galacto-hept-1-enitol 在 mercury(II) diacetate 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 以91%的产率得到2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-iodo-D-glycero-L-galacto-heptitol
  参考文献：
  名称：

  Synthesis of D-Galactopyranosylphosphonic and (D-Galactopyranosylmethyl)phosphonic Acids as Intermediates of Inhibitors of Galactosyltransferases

  摘要：

  采用1-O-乙酰基-2,3,4,6-四-O-苄基-D-半乳糖吡喃糖与三乙基膦酸酯和三甲基硅基三氟甲磺酸酯的Michaelis-Arbuzov反应，分别以33%和28%的收率制备了α-和β-D-半乳糖吡喃糖基膦酸。(α-D-半乳糖吡喃糖基甲基)膦酸是通过从2,3,4,6-四-O-苄基-D-半乳糖吡喃糖出发的五步路线合成的，总收率为52%。在测试对牛α-1,3-和β-1,4-半乳糖基转移酶的抑制作用时，所有三种化合物显示出的抑制作用都很弱。两种酶都更有效地被β-D-半乳糖吡喃糖基膦酸抑制（IC₅₀ = 17 mmol l^-1，在13.5 μmol l^-1的UDP-半乳糖浓度下对β4GalT）。

  DOI：

  10.1135/cccc20061659
• 作为产物：
  描述：

  p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 21.83h， 生成 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-galacto-hept-1-enitol
  参考文献：
  名称：

  Synthetic Iminosugar Derivatives as New Potential Immunosuppressive Agents

  摘要：

  Several iminosugar derivatives were synthesized, and their effects on the secretion of IL-4 and IFN-gamma from the mouse splenocytes were examined. The effects on membrane expression of other T cell-associated molecules (CD3, CD4, CD8) and B cell-associated molecules (CD19) were also investigated. The experimental data demonstrated that synthetic iminosugars hold potential as immunosuppressive agents.

  DOI：

  10.1021/jm050169t

文献信息

• Intramolecular ketonitrone-olefin cycloaddition reaction: direct and stereocontrolled synthesis of nitrogenated quaternary centered aminocyclopentitols as galactosidase inhibitors
  作者：Y. Suman Reddy、P. Kadigachalam、Venkata Ramana Doddi、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2009.07.157

  日期：2009.10

  Synthesis of nitrogenated quaternary centered polyhydroxylated aminocyclopentanes by implementation of ketonitrone-olefin cycloaddition reaction as a key step has been accomplished in a stereocontrolled manner. The target molecules were found to be moderate but selective inhibitors of galactosidases.

  作为关键步骤，通过进行酮硝基-烯烃环加成反应来合成硝化的季中心多羟基化的氨基环戊烷已经以立体控制的方式完成。发现目标分子是半乳糖苷酶的中度但选择性抑制剂。
• An efficient synthetic approach to aza-C-glycosyl compounds. Application to the synthesis of an aza-C-disaccharide
  作者：Olivier R. Martin、Li Liu、Feng Yang

  DOI：10.1016/0040-4039(96)00226-2

  日期：1996.3

  aminoheptenitols 5–8 (prepared in three steps from ) provided 1,2,6-trideoxy-2,6-imino-liodoheptitol derivatives 9–12, respectively, highly stereoselectively and in high yield. The “” epimer 9 was used in the synthesis of a precursor of an aza-C-disacharide and its reaction with triethyl phosphite was investigated.

  NIS介导的氨基庚糖醇5-8的环化反应（从制备三个步骤开始）分别提供了1,2,6-丁氧基-2,6-亚氨基碘代庚糖醇衍生物9-12，具有高立体选择性和高收率。将“ ”差向异构体9用于合成氮杂-C-二糖苷的前体，并研究了其与亚磷酸三乙酯的反应。
• Stereospecific cyclization to form C-furanosides
  作者：Bing-Hui Yang、Ji-Qing Jiang、Kan Ma、Hou-Ming Wu

  DOI：10.1016/0040-4039(95)00413-7

  日期：1995.4

  A cyclization of benzyl ethers with Sn2 active site at γ-position to form C-furanoside was studied.

  研究了在γ位具有S n 2活性位的苄基醚的环化反应，形成C-呋喃糖苷。
• Enzyme-catalyzed synthesis of isosteric phosphono-analogues of sugar nucleotides
  作者：Stephen A. Beaton、Malcolm P. Huestis、Ali Sadeghi-Khomami、Neil R. Thomas、David L. Jakeman

  DOI：10.1039/b808078j

  日期：——

  Efficient enzymatic syntheses of isosteric phosphono analogues of sugar nucleotides have been accomplished using a thymidylyltransferase.

  利用胸苷酰基转移酶，已经成功实现了糖核苷酸等效磷酸类似物的酶促高效合成。
• Total synthesis of carbocyclic nucleoside (+)-neplanocin A
  作者：Young Hoon Jung、Seung In Kim、Yeon Ju Hong、Sook Jin Park、Kyung Tae Kang、So Yeon Kim、In Su Kim

  DOI：10.1016/j.tet.2014.12.093

  日期：2015.2

  Asymmetric total synthesis of (+)-neplanocin A was concisely achieved from readily available d-galactose via the regioselective and diastereoselective amination of carbocyclic polybenzyl ether using chlorosulfonyl isocyanate and intramolecular olefin metathesis using second-generation Grubbs catalyst.

  使用氯磺酰基异氰酸酯通过碳环聚苄基醚的区域选择性和非对映选择性胺化以及使用第二代Grubbs催化剂进行的分子内烯烃复分解，从易于获得的d-半乳糖简明地实现了（+）-neplanocin A的不对称全合成。