(2R,3S,4S,5R)-2,3,4-tri-benzyloxy-5-benzyloxymethyl-cyclohexanone | 924298-43-1

• 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: (2R,3S,4S,5R)-2,3,4-tri-benzyloxy-5-benzyloxymethyl-cyclohexanone
• CAS: 924298-43-1
• 化学式: C₃₅H₃₆O₅
• 分子量: 536.668
• InChiKey: SUNQRZNLNFNHJL-PEBYJJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-2,3,4-tri-benzyloxy-5-benzyloxymethyl-cyclohexanone 、 (2S,3R,4E)-3-benzyloxy-1,2-(p-tolylsulfonylimino)-4-octadecene 在 L-Selectride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以85%的产率得到(2S,3R,4E)-3-benzyloxy-1-(2',3',4',6'-tetra-O-benzyl-5a-carba-α-D-galactopyranosyloxy)-2-(p-toluenesulfonylamino)-4-octadecene
  参考文献：
  名称：

  Practical syntheses of optically active carbagalactose and their potential application to the carbocyclic analogues of KRN7000

  摘要：

  Carba-alpha- and beta-D-galactose derivatives were efficiently prepared from a cyclohex-3-ene-1,2-diol derivative 1. Regioselective inversion of 2-OH, and stereoselective dihydroxylation of I were accomplished to provide a carba-p-D-galactose derivative 6 in a good yield and with a high stereoselectivity. Stereo-inversion of 1-OH of 6 via oxidation/reduction gave carba-beta-D-galactose derivative 12 with a high stereoselectivity. An efficient coupling of carba-alpha-galactose 12 with an aziridine derivative of sphingosine has been demonstrated to give 1-O-carba-alpha-galactosyl sphingosine derivative 14. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.014
• 作为产物：
  描述：

  (1R,2S,5S)-5-(tert-butyl-diphenylsilanyloxymethyl)-1-(methoxymethoxy)-2-p-nitrobenzoyloxy-cyclohex-3-ene 在 盐酸 、 四氧化锇 、 4 A molecular sieve 、 四丁基氟化铵 、 水 、 sodium methylate 、 sodium hydride 、 N-甲基吗啉氧化物 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 88.08h， 生成 (2R,3S,4S,5R)-2,3,4-tri-benzyloxy-5-benzyloxymethyl-cyclohexanone
  参考文献：
  名称：

  Practical syntheses of optically active carbagalactose and their potential application to the carbocyclic analogues of KRN7000

  摘要：

  Carba-alpha- and beta-D-galactose derivatives were efficiently prepared from a cyclohex-3-ene-1,2-diol derivative 1. Regioselective inversion of 2-OH, and stereoselective dihydroxylation of I were accomplished to provide a carba-p-D-galactose derivative 6 in a good yield and with a high stereoselectivity. Stereo-inversion of 1-OH of 6 via oxidation/reduction gave carba-beta-D-galactose derivative 12 with a high stereoselectivity. An efficient coupling of carba-alpha-galactose 12 with an aziridine derivative of sphingosine has been demonstrated to give 1-O-carba-alpha-galactosyl sphingosine derivative 14. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.014

文献信息

• Galacto-Configured Aminocyclitol Phytoceramides Are Potent in Vivo Invariant Natural Killer T Cell Stimulators
  作者：Youssef Harrak、Carolina M. Barra、Antonio Delgado、A. Raúl Castaño、Amadeu Llebaria

  DOI：10.1021/ja202610x

  日期：2011.8.10

  A new class of a-galactosylceramide (alpha GC) nonglycosidic analogues bearing galacto-configured aminocyclitols as sugar surrogates have been obtained. The aminocyclohexane having a hydroxyl substitution pattern similar to an a-galactoside is efficiently obtained by a sequence involving Evans aldol reaction and ring-closing metathesis with a Grubbs catalyst to give a key intermediate cyclohexene, which has been converted in galacto-aminocyclohexanes that are linked through a secondary amine to a phytoceramide lipid having a cerotyl N-acyl group. Natural Killer T (NKT) cellular assays have resulted in the identification of an active compound, HS161, which has been found to promote NKT cell expansion in vitro in a similar fashion but more weakly than alpha GC. This compound stimulates the release of Interferon-gamma (IFN gamma) and Interleukin-4 (IL-4) in iNKT cell culture but with lower potency than alpha GC. The activation of Invariant Natural Killer T (iNKT) cells by this compound has been confirmed in flow cytometry experiments. Remarkably, when tested in mice, HS161 selectively induces a very strong production of IFN-gamma indicative of a potent Th1 cytokine profile. Overall, these data confirm the agonist activity of alpha GC lipid analogues having charged amino-substituted polar heads and their capacity to modulate the response arising from iNKT cell activation in vivo.