isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside | 440652-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranoside；isopropyl-2,3,4,5-tetra-O-benzyl-1-thio-β-D-galactopyranoside；(2R,3S,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-propan-2-ylsulfanyloxane
• CAS: 440652-81-3
• 化学式: C₃₇H₄₂O₅S
• 分子量: 598.803
• InChiKey: VDFFPQCRIYDVDM-AESTUDHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 在 甲醇 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 dodecyl β-D-galactopyranoside
  参考文献：
  名称：

  Sweet surfactants: packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles

  摘要：

  对异构体对两性分子性质（如乳化和作为纳米粒子生长调节剂）的影响进行探索，使用基于糖苷的表面活性剂库。

  DOI：

  10.1039/c8sm01091a
• 作为产物：
  描述：

  [(2R,3R,4S,5S,6R)-3,4,5-三苄氧基-6-(苄氧基甲基)四氢吡喃-2-基]2,2,2-三氯乙亚氨酸酯 、 异丙硫醇 在 二氟苯基硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.2h， 以72%的产率得到isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  在酸/碱催化下用 O-糖基三氯乙酰亚胺酯作为糖基供体和硫醇作为受体逆转异头异构选择性

  摘要：

  三氟化硼或三甲基甲硅烷基三氟甲磺酸酯催化从 O-吡喃葡萄糖基或 O-吡喃半乳糖基三氯乙酰亚胺酯和硫醇生成硫糖苷，主要或仅产生 α-硫糖苷。然而，与作为催化剂的苯基二氟化硼的相同反应是高度β-选择性的。这些和以前的结果引发了酸/碱催化下的 SN2 型反应过程。

  DOI：

  10.1002/ejoc.201200138

文献信息

• A simple access to 3,6-branched oligosaccharides: Synthesis of a glycopeptide derivative that relates to Lycium barbarum L.
  作者：Yuguo Du、Meimei Zhang、Feng Yang、Guofeng Gu

  DOI：10.1039/b108399f

  日期：2001.11.29

  An efficient method is described for the synthesis of galactopyranosyl-containing 3,6-branched oligosaccharides using isopropyl thiogalactopyranoside as starting material. This method is successfully applied to the preparation of a glycopeptide derivative that relates to Lycium barbarum L. The potential application of isopropyl thioglycoside in glycosylation is also investigated.

  本研究介绍了一种以异丙基硫代吡喃半乳糖苷为起始原料合成含吡喃半乳糖基的 3,6 支链低聚糖的有效方法。该方法被成功应用于制备一种与枸杞有关的糖肽衍生物，同时还研究了异丙基硫代糖苷在糖基化中的潜在应用。
• New potent insecticidal agent: 4′-fucosyl avermectin derivative
  作者：Guohua Wei、Yuguo Du、Robert J. Linhardt

  DOI：10.1016/j.tetlet.2004.07.092

  日期：2004.9

  A 4′-fucosyl avermectin derivative was designed and synthesized. This new avermectin derivative showed excellent in vivo bioactivity against cabbage larvae when compared to commercially available avermectin B1a. In this synthesis, thioglycosyl donors, but not trichloroacetimidates, were found compatible with sugar-macrolide synthesis under rt promotion with NIS or I2 in N-methylpyrrolidone.

  设计合成了一个4'-岩藻糖基阿维菌素衍生物。与市售的阿维菌素B 1a相比，这种新的阿维菌素衍生物对白菜幼虫具有优异的体内生物活性。在该合成中，发现在硫代糖基供体而不是三氯乙酰亚氨酸酯与糖-大环内酯合成相容，在室温下用NIS或I 2在N-甲基吡咯烷酮中促进。
• First synthesis of 5,6-branched galacto-hexasaccharide, the dimer of the trisaccharide repeating unit of the cell-wall galactans of Bifidobacterium catenulatum YIT 4016
  作者：Guohua Zhang、Mingkun Fu、Jun Ning

  DOI：10.1016/j.tetasy.2004.12.014

  日期：2005.2

  alpha-D-Galactopyranosyl-(1 --> 6)-[beta-D-galactofuranosyl-(1 --> 5)]-beta-D-galactofuranosyl-(1 --> 6)-beta-D-galactofuranosyl-(1 --> 5)-[alpha-D -galactopyranosyl-(1 --> 6)]-beta-D-galactofuranose, the dimer of the trisaccharide repeating unit of the cell-wall galactans of Bifidobacterium catenulatum YIT 4016, has been synthesized as its dodecyl glycoside 2 by coupling of 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1 --> 6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)]-2-O-acetyl-3-O-benzyl-beta-D-galactofuranosyl trichloroacetimidate 14 with dodecyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1 --> 6)-[2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)]-2-O-acetyl-3-O-benzyl-beta-D-galactofuranoside 16. The trisaccharide trichloroacetimidate donor 14 and trisaccharide acceptor 16 were regiospecifically prepared by employing 3-O-benzyl-1,2-O-isopropylidene-alpha-D-galactofuranose 4 as the glycosyl acceptor, and isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside 5 and 6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl trichloroacetimidate 9 as glycosyl donors. (C) 2005 Elsevier Ltd. All rights reserved.
• CN114805454
  申请人：——

  公开号：——

  公开（公告）日：——
• Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis
  作者：Amit Kumar、Richard R. Schmidt

  DOI：10.1002/ejoc.201200138

  日期：2012.5

  Boron trifluoride or trimethylsilyl trifluoromethanesulfonate catalysed the generation of thioglycosides from O-glucopyranosyl or O-galactopyranosyl trichloroacetimidates and thiols giving mainly or exclusively α-thioglycosides. However, the same reactions with phenylboron difluoride as catalyst are highly β-selective. An SN2-type reaction course under acid/base catalysis is invoked by these and previous

  三氟化硼或三甲基甲硅烷基三氟甲磺酸酯催化从 O-吡喃葡萄糖基或 O-吡喃半乳糖基三氯乙酰亚胺酯和硫醇生成硫糖苷，主要或仅产生 α-硫糖苷。然而，与作为催化剂的苯基二氟化硼的相同反应是高度β-选择性的。这些和以前的结果引发了酸/碱催化下的 SN2 型反应过程。