(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol | 105938-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
• 英文别名: 2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-glycero-D-gulo-heptitol；(2S,3S,4R,5R,6R)-2-methyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 105938-03-2
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: HTBCIOACXYNFLJ-KNQFCDCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol 在 乙酸酐 、 二甲基亚砜 作用下， 生成 (2S,4S,5R,6R)-2-methyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-one
  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
• 作为产物：
  描述：

  三-O-(叔丁基二甲基甲硅烷基)-D-葡萄烯糖 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 作用下， 生成 (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  通过异头中心的极性反转形成C-糖苷

  摘要：

  经由相应的1-三丁基锡烷基衍生物获得的1-硫代三取代糖基的烷基化构成了新的进入C-糖苷的方法。

  DOI：

  10.1039/c39860000926

文献信息

• Preparation and Transmetallation of a Triphenylstannyl ?-D-Glucopyranoside: A highly stereoselective route to ?-D-C-glycosidesvia glycosyl dianions
  作者：Oliver Frey、Matthias Hoffmann、Valentin Wittmann、Horst Kessler、Peter Uhlmann、Andrea Vasella

  DOI：10.1002/hlca.19940770730

  日期：1994.11.2

  The triphenylstannyl β-D-glucopyranoside 4 was synthesized in one step from the 1,2-anhydro-α-D-glucopyranose 3 with (triphenylstannyl)lithium (Scheme 1). Transmetallation of 4 with excess BuLi, followed by quenching the dianion 7 with CD3OD gave (1S)-1,5-anhydro-3,4,6-tri-O-benzyl-[1-2H]-D- glucitol (8) in 81% yield (Scheme 2). Trapping of 7 with benzaldehyde, isobutyraldehyde, or acroleine gave the

  由1,2-脱水-α-D-吡喃葡萄糖3与（三苯基锡烷基）锂一步合成三苯基锡烷基β-D-吡喃葡萄糖苷4（方案1）。的金属转移4用过量的丁基锂，随后淬火二价阴离子7与CD 3 OD，得到（1个小号）-1,5-脱水-3,4,6-三ö苄基- [1- 2 H] -D-葡萄糖醇（8），产率为81％（方案2）。用苯甲醛，异丁醛或丙烯醛诱捕7得到预期的β-D构型的产物11、12和13丰产。由酰基氯例如乙酰基或苯甲酰氯制备C-酰基糖苷是不可行的，但是将苯甲腈添加到7中产生84％的苯甲酰化产物14。用MeI处理7导致15（30％）以及18的40％，C-烷基化伴随卤素-金属交换。预先加入锂2- thienylcyanocuprate的的产率增加15％至50％，并使用硫酸二甲酯代替将MeI导致77％15。除了使用烯丙基溴作为亲电试剂以外，没有检测到α-D-异头物，它以1：1的异构体混合物形式生成16和17。
• C-Glycosides to fused polycyclic ethers
  作者：Shawn P. Allwein、Jason M. Cox、Brett E. Howard、Henry W.B. Johnson、Jon D. Rainier

  DOI：10.1016/s0040-4020(02)00057-1

  日期：2002.3

  This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions. (C) 2002 Elsevier Science 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.
• Formation of C-glycosides by polarity inversion at the anomeric centre
  作者：S. Hanessian、M. Martin、R. C. Desai

  DOI：10.1039/c39860000926

  日期：——

  Alkylation of 1-lithio trisubstituted glycals obtained via the corresponding 1-tributylstannyl derivatives constitutes a novel entry into C-glycosides.

  经由相应的1-三丁基锡烷基衍生物获得的1-硫代三取代糖基的烷基化构成了新的进入C-糖苷的方法。