3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene | 192929-31-0

• 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: 3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene
• 英文别名: (2S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enyloxan-3-one
• CAS: 192929-31-0
• 化学式: C₃₀H₃₂O₅
• 分子量: 472.581
• InChiKey: JJOOLDPCJMXIJA-UGWFNHDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以78%的产率得到3-C-(3,6-di-O-benzyl-4-deoxy-β-D-glycero-2-ulopyranosyl)propene
  参考文献：
  名称：

  Multifunctionalized α,β-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: a stereospecific rearrangement initiated by base

  摘要：

  Base treatment of O-benzyl protected C-2- or C-4-ulopyranosyl compounds (4 alpha, 4 beta, and 11) by either 10% Et3N or 1% K2CO3 in MeOH initiated a beta elimination to afford alpha,beta-unsaturated C-ulopyranosyl compounds (5 alpha, 5 beta, and 12), which further rearranged in a stereocontrolled manner to multifuctionalized alpha,beta-cyclopentenones (6 and 14) in 70-80% yield. Both C-alpha- and C-beta-2-ulosides (5 alpha and 5 beta) produced the same cyclopentenone 6, indicating that a 1,2-enolate is formed prior to the cleavage of the C-5-O bond. Because 6 is racemic, it was probably formed by the intramolecular cycloaldolization of two equally populated enantiomeric intermediates. When treated with 90% Et3N in MeOH, 5 alpha yielded almost exclusively 15 (isomer of 6), which was formed by a migration of the double bond in 5 alpha during the previously described rearrangement. Thus either 6 or 15 was the major product, depending on the base used. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00187-2
• 作为产物：
  描述：

  (3R,4R,5S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]heptane 在 乙酸酐 、 二甲基亚砜 作用下， 以 乙醚 为溶剂， 生成 3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene
  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

• Synthesis of 2-Deoxy-2-<i>C</i>-alkyl Glycal and Glycopyranosides from 2-Hydroxy Glycal Ester
  作者：Gour Chand Daskhan、Narayanaswamy Jayaraman

  DOI：10.1021/jo202240f

  日期：2012.3.2

  glycal ester to the corresponding 2-deoxy-2-C-alkyl glycal in a facile manner, through key reactions including (i) C-allylation at C-1, (ii) Wittig reaction, and (iii) Cope rearrangement of a 1,5-diene derivative, is reported. The α-anomer of the 1,5-diene derivative underwent Cope rearrangement to afford 2-deoxy-2-C-glycal derivative, whereas the β-anomer was found to be unreactive. Employing this sequence

  的方法，2-羟基烯糖酯转化成相应的2-脱氧-2- Ç烷基烯糖以容易的方式，通过关键反应包括：（i）C ^ -allylation在Ç -1，（ⅱ）Wittig反应，和（ iii）报道了应对1，5-二烯衍生物的重排。对1，5-二烯衍生物的α-端基异构体进行Cope重排，得到2-脱氧-2- C-糖基衍生物，而发现β-端基异构体没有反应性。使用该序列中，3,4,6-三- ø -苄基-2- ø -乙酰基-1,5-脱水- d -阿拉伯糖-己-1- enitol转化到3,4,6-三ö -苄基-2-脱氧-2- C-烷基-1,5-脱水-d -阿拉伯糖-己-1- enitol。2-脱氧-2- C-烷基糖基衍生物是制备2-脱氧-2- C-烷基糖苷的合适的糖基供体，其通过卤代糖基化和随后的脱卤作用而介导。因此由该糖基制备了许多2-还原氧基-2- C-烷基糖苷，在还原端具有糖基和非糖基部分。
• Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells
  作者：Carlos A. Sanhueza、Carlos Mayato、María García-Chicano、Raquel Díaz-Peñate、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2006.05.079

  日期：2006.8

  A large series of alkyl C-glycosides was synthesized from D-glucal or D-galactal. These compounds were screened against the human promyelocytic leukemia cell line (HL60), showing significant activity and apoptosis. Up to 13 C-glucopyranosides, but no C-galacto- or C-mannopyranosides, exhibited inhibitory concentrations (IC50 values) below 20 mu M, five of them in the range 4-8 mu M. Preliminary structure-activity relationships were established. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors
  作者：Venkata Ramana Doddi、Pavan K. Kancharla、Y. Suman Reddy、Amit Kumar、Yashwant D. Vankar

  DOI：10.1016/j.carres.2009.01.017

  日期：2009.3

  Synthesis of polyhydroxylated oxabicyclo[4,4,0]decanes, which constitute a new family of annulated carbasugars, has been accomplished in a stereoselective manner by employing readily available 1,2-anhydro-3,4,6-tri-O-benzyl-alpha-D-glycopyranoses. (C) 2009 Elsevier Ltd. All rights reserved.
• New and Easy Access to C-Glycosides of Glucosamine and Mannosamine
  作者：Laura Cipolla、Luigi Lay、Francesco Nicotra

  DOI：10.1021/jo970127f

  日期：1997.9.1
• 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.