p-methylphenyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside | 323195-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: p-methylphenyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
• 英文别名: 2,2,2-trichloroethyl N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-(4-methylphenyl)sulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate
• CAS: 323195-39-7
• 化学式: C₁₉H₂₄Cl₃NO₆S
• 分子量: 500.828
• InChiKey: NOJPCVHSPTXONB-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 在 四溴化碳 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到p-methylphenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions

  摘要：

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.095
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 p-methylphenyl 2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  β-D-吡喃葡萄糖基(1→3)-1-硫醇-β-葡糖胺二糖衍生物的合成作为透明质酸合成的构件

  摘要：

  描述了标题二糖 2 的实用合成方法。使用硫代糖苷作为受体，糖基亚胺酸酯作为供体，使用三甲基甲硅烷基四氟甲磺酸盐作为促进剂进行糖基化。

  DOI：

  10.1002/jccs.200000125

文献信息

• pH Dependent Thermal Stabilization of DNA by Glcβ(1→3)GlcNAcβ1→STol
  作者：Chun-Cheng Lin、Sue-Mei Hung、Kuo-Cheng Lu、Chien-Chung Cheng

  DOI：10.1002/jccs.200400098

  日期：2004.6

  A disaccharide, Glc)(1→3)GlcNAcβ1→STol (GGS, 1), was synthesized and demonstrated to stabilize ct-DNA during the denaturing process. GGS at 50 μM shifted T m of ct-DNA by 23 °C and the behavior was pH dependent. Poly(dA-dT) 2 was found to be the preferable type of DNA for GGS stabilization by circular dichroism spectroscopy study.

  合成了一种二糖 Glc)(1→3)GlcNAcβ1→STol (GGS, 1)，并证明它可以在变性过程中稳定 ct-DNA。50 μM 的 GGS 将 ct-DNA 的 T m 移动了 23 °C，其行为取决于 pH。通过圆二色光谱研究发现 Poly(dA-dT) 2 是用于稳定 GGS 的优选 DNA 类型。
• Simple and efficient per-O-acetylation of carbohydrates by lithium perchlorate catalyst
  作者：Kuo-Cheng Lu、Shu-Yi Hsieh、Laxmikant N. Patkar、Chien-Tien Chen、Chun-Cheng Lin

  DOI：10.1016/j.tet.2004.06.138

  日期：2004.9

  Lithium perchlorate is demonstrated to be a highly efficient and convenient catalyst for the per-O-acetylation of various saccharides with excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.
• O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate
  作者：Chun-Cheng Lin、Mi-Dan Jan、Shiue-Shien Weng、Chang-Ching Lin、Chien-Tien Chen

  DOI：10.1016/j.carres.2006.04.001

  日期：2006.8

  Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of β-<scp>D</scp>-Glucopyranosyl(1→3)-1-thiol-β-glucosamine Disaccharide Derivative as Building Block for the Synthesis of Hyaluronic Acid
  作者：Chun-Cheng Lin、Tzu-Sui Hsu、Kuo-Cheng Lu、I-Ting Huang

  DOI：10.1002/jccs.200000125

  日期：2000.8

  A practical synthetic method for the title disaccharide 2 is described. Glycosylation using thioglycoside as acceptor and glycosyl imidate as donor was performed with trimethylsilyltriflate as the promoter.

  描述了标题二糖 2 的实用合成方法。使用硫代糖苷作为受体，糖基亚胺酸酯作为供体，使用三甲基甲硅烷基四氟甲磺酸盐作为促进剂进行糖基化。
• Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions
  作者：Ming-Yi Chen、Laxmikant N. Patkar、Kuo-Cheng Lu、Adam Shih-Yuan Lee、Chun-Cheng Lin

  DOI：10.1016/j.tet.2004.09.095

  日期：2004.12

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.