3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol | 288584-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol
• 英文别名: (2S,3S,4R,5R,6R)-2-(3-hydroxypropyl)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 288584-96-3
• 化学式: C₃₀H₃₆O₆
• 分子量: 492.612
• InChiKey: AJQSWXHARPGOIM-PGVCKJCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 氘代三正丁基锡 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲苯 为溶剂， 反应 6.0h， 生成 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propanol
  参考文献：
  名称：

  1,5-氢原子转移/Surzur-Tanner 重排：在碳水化合物系统中合成 1,6-二氧杂螺[4.5]癸烷和 6,8-二氧杂双环[3.2.1]辛烷支架的自由基级联方法

  摘要：

  已经在一系列具有 3 -C- ( α, β- d , l - 吡喃葡萄糖基）1-丙醇和C -（α- d , l -吡喃葡萄糖基）甲醇结构，由手性池d - 和l - 糖制备。使用乙酰氧基和二苯氧基磷酸酯氧基作为离去基团可有效构建 10-deoxy-1,6-dioxaspiro[4.5]decane 和 4-deoxy-6,8-dioxabicyclo[3.2.1]octane 骨架。烷氧基自由基由相应的N反应生成-烷氧基邻苯二甲酰亚胺与第 14 族氢化物 [ n -Bu 3 SnH(D) 和 (TMS) 3 SiH]，比较而言，该反应也由使用 Hantzsch 酯/ fac -Ir(ppy) 3程序的可见光光催化引发. 特别关注自由基序列中涉及的中心的相对立体化学对反应结果的影响。将BF 3 •Et 2 O 作为催化剂添加到自由基序列中导致所需双环缩酮的产率显着增加。

  DOI：

  10.1021/acs.joc.1c01376
• 作为产物：
  描述：

  (3R,4R,5S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]heptane 在 dimethyl sulfide borane 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol
  参考文献：
  名称：

  Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

  摘要：

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.060

文献信息

• Stereoselective synthesis of α- and β-C-glucosides via radical cyclization with an allylsilyl tether. Control of the stereoselectivity by changing the conformation of the pyranose ring
  作者：Satoshi Shuto、Masaru Terauchi、Yumi Yahiro、Hiroshi Abe、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1016/s0040-4039(00)00556-6

  日期：2000.5

  An efficient method for preparing both 1α- and 1β-C-glucosides having a 3-hydroxypropyl group at the anomeric position via a radical cyclization reaction with an allylsilyl tether was developed. The stereoselectivity of the radical cyclization can be controlled by the conformation of the pyranose ring, which is effectively manipulated by the hyroxyl protecting groups.

  开发了一种通过与烯丙基甲硅烷基系链的自由基环化反应制备在异头位置具有3-羟丙基的1α-和1β- C-葡糖苷的有效方法。自由基环化的立体选择性可以通过吡喃糖环的构象来控制，吡喃糖环的构象可以被羟基保护基有效地操纵。
• Diisobutylaluminium hydride (DIBAL-H) as a molecular scalpel: a new mechanistic proposal for a spiroketal rearrangement
  作者：Xiangbao Meng、Yongmin Zhang、Matthieu Sollogoub、Pierre Sinaÿ

  DOI：10.1016/j.tetlet.2004.09.030

  日期：2004.10

  Taking advantage of our knowledge of the capacity of DIBAL-H to de-O-alkylate, we propose an alternative mechanism for a spiroketal rearrangement described by E. Suàrez. We also show that this proposal can account for the formation of the secondary product, whose original structure we propose to correct.

  利用我们对DIBAL-H脱O-烷基化能力的认识，我们提出了E.Suàrez所描述的螺环重排的另一种机制。我们还表明，该提议可以解释次级产品的形成，我们建议更正其原始结构。
• Synthesis of 4,8-anhydro-d-glycero-d-ido-nonanitol 1,6,7-trisphosphate as a novel IP3 receptor ligand using a stereoselective radical cyclization reaction based on a conformational restriction strategy
  作者：Masaru Terauchi、Yumi Yahiro、Hiroshi Abe、Satoshi Ichikawa、Stephen C. Tovey、Skarlatos G. Dedos、Colin W. Taylor、Barry V.L. Potter、Akira Matsuda、Satoshi Shuto

  DOI：10.1016/j.tet.2005.02.025

  日期：2005.4

  4,8-Anhydro-D-glycero-D-ido-nonanitol 1,6,7-trisphosphate (9), designed as a novel IP3 receptor ligand having an alpha-C-glycosidic\ structure, was synthesized via a radical cyclization reaction with a temporary connecting allylsilyl group as the key-step. Phenyl 2-O-allyldimethylsilyt-3,4-bis-O-TBS-1-seleno- beta-D-glucopyranoside (10a), conformationally restricted in the unusual C-1(4)-conformation, was treated with Bu3SnH/AIBN to form the desired alpha-cyclization product 16a almost quantitatively. On the other hand, when a conformationally unrestricted O-benzyl-protected 2-O-allyldimethylsilyl -l-selenoglucoside 15 was used as the substrate, the radical reaction was not stereoselective and gave a mixture of the alpha-and beta-products. From 16a, the target C-glucoside trisphosphate 9 was synthesized via phosphorylation of the hydroxyls by the phosphoramidite method. During the synthetic study, an efficient procedure for the oxidative C-Si bond cleavage, via a nucleophilic substitution at the silicon with p-MeOPhLi followed by Fleming oxidation, was developed. The C-glycoside 9 was found to be a full agonist for Ca2+ mobilization, although its activity was weaker than that of the natural ligand IP3. Thus, the alpha-C-glucosidic structure was shown to be a useful mimic of the myo-inositol backbone of IP3. (c) 2005 Elsevier Ltd. All rights reserved.
• A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin
  作者：Isao Kadota、Takashi Abe、Miyuki Uni、Hiroyoshi Takamura、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2008.03.145

  日期：2008.5

  Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring. (C) 2008 Elsevier Ltd. All rights reserved.
• Cytotoxic effects of C-glycosides in HOS and HeLa cell lines
  作者：Carlos A. Sanhueza、Carlos Mayato、Rubén P. Machı´n、José M. Padrón、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2007.04.060

  日期：2007.7

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.