1-吖丁啶羧酸,3-[(2-溴苯基)磺酰]-,1,1-二甲基乙基酯 | 7534-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-吖丁啶羧酸,3-[(2-溴苯基)磺酰]-,1,1-二甲基乙基酯
• 英文名称: 1-thio-β-D-glucopyranose
• 英文别名: 1-thio-β-D-glucose；thioglucose；1-Thio-beta-D-glucopyranose；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-sulfanyloxane-3,4,5-triol
• CAS: 7534-35-2
• 化学式: C₆H₁₂O₅S
• 分子量: 196.224
• InChiKey: JUSMHIGDXPKSID-DVKNGEFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.2
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-吖丁啶羧酸,3-[(2-溴苯基)磺酰]-,1,1-二甲基乙基酯 在 glucose oxidase 作用下， 以 重水 为溶剂， 反应 2.0h， 生成 葡糖酸
  参考文献：
  名称：

  A Sweet H₂S/H₂O₂ Dual Release System and Specific Protein S-Persulfidation Mediated by Thioglucose/Glucose Oxidase

  摘要：

  DOI：

  10.1021/jacs.1c06372
• 作为产物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以78%的产率得到1-吖丁啶羧酸,3-[(2-溴苯基)磺酰]-,1,1-二甲基乙基酯
  参考文献：
  名称：

  Micelles based on gold-glycopolymer complexes as new chemotherapy drug delivery agents

  摘要：

  通过对 RAFT 糖聚合物进行后修饰，制备出了去乙酰化金配体（一种带有糖配体的金复合物）的聚合物版本。将含有悬垂金（I）单元的嵌段共聚物进行胶束化处理，制备出了对 OVCAR-3 人类卵巢癌细胞具有更强抗增殖作用的纳米粒子。

  DOI：

  10.1039/c2cc30510k
• 作为试剂：
  描述：

  3-dimethoxyphosphanylpropenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 1-吖丁啶羧酸,3-[(2-溴苯基)磺酰]-,1,1-二甲基乙基酯 、 安息香双甲醚 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到3-dimethoxyphosphanylpropenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Metal-free synthesis of E-vinylphosphonates via photoinduced alkyne hydrophosphonylation and thiol promoted isomerization sequence

  摘要：

  The alkyne hydrophosphonylation is an atom economical method for the synthesis of vinylphosphonates that are compounds of both biological and synthetic relevance. Recent approaches based on the use of metal catalysts have only partially solved the problems of the reaction selectivity as well as of economical and large amount production. We report in this Letter on a metal-free approach that leads to E-vinylphosphonates in high yields. The approach is based on a two-step one-pot synthesis, namely: (a) photoinduced anti-Markovnikov addition of a H-phosphonate to alkynes to give mixtures of E- and Z-vinylphosphonates, and (b) cysteine promoted photoinduced conversion of the crude mixtures of adducts into E-isomers (58-92% overall yields). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.099

文献信息

• Stereoselective Palladium-Catalyzed Alkenylation and Alkynylation of Thioglycosides
  作者：Etienne Brachet、Jean-Daniel Brion、Mouad Alami、Samir Messaoudi

  DOI：10.1002/adsc.201300419

  日期：2013.9.16

  An efficient and unprecedented palladium‐catalyzed S‐glycosylation reaction of a range of alkenyl and alkynyl halides by using thiosugars as nucleophile partners has been established. With palladium diacetate in combination with Xantphos as the catalytic system, a variety of β‐alkenylthioglycosides as well as β‐alkynylthioglycosides can be prepared in good to excellent yields. The efficiency of this

  通过使用硫糖作为亲核试剂的伙伴，已经建立了有效且前所未有的钯催化的一系列链烯基和炔基卤化物的S-糖基化反应。将二乙酸钯与Xantphos结合用作催化体系，可以制备各种β-烯基硫代糖苷以及β-炔基硫代糖苷，而且收率很高。叶片封闭的β-葡萄糖苷酶抑制剂的正式合成充分证明了该通用方案的有效性。
• Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides
  作者：Mingxiang Zhu、Mouad Alami、Samir Messaoudi

  DOI：10.1039/d0cc01126f

  日期：——

  Here we report a simple route towards the synthesis of thioglycosides, in which electrochemical cross-coupling is used to form a S-C glycosidic bond from protected and unprotected thiosugars with functionalized aryl bromides under base free conditions. The reaction manifold that we report here demonstrates the power of electrochemistry to access highly complex glycosides under mild conditions.

  在这里，我们报告了一种简单的合成硫糖苷的方法，其中电化学交叉偶联用于在无碱条件下由受保护和未受保护的硫糖与功能化的芳基溴化物形成SC糖苷键。我们在此报告的反应歧管证明了在温和条件下电化学作用可获取高度复杂的糖苷的能力。
• Biomimetic studies on the mechanism of stereoselective lanthionine formationElectronic supplementary information (ESI) available: separation of the diastereomers of 5; cleavage of peptides from resins; COSY NMR spectrum of the product obtained from cyclization of both E-1 and 19. See http://www.rsc.org/suppdata/ob/b3/b304945k/
  作者：Yantao Zhu、Matt D. Gieselman、Hao Zhou、Olga Averin、Wilfred A. van der Donk

  DOI：10.1039/b304945k

  日期：——

  Selenocysteine derivatives are useful precursors for the synthesis of peptide conjugates and selenopeptides. Several diastereomers of Fmoc-3-methyl-Se-phenylselenocysteine (FmocMeSec(Ph)) were prepared and used in solid phase peptide synthesis (SPPS). Once incorporated into peptides, the phenylselenide functionality provides a useful handle for the site and stereospecific introduction of E- or Z-dehydrobutyrine

  硒代半胱氨酸衍生物是用于合成肽缀合物和硒肽的有用前体。制备了Fmoc-3-甲基-Se-苯基硒代半胱氨酸的几种非对映异构体（FmocMeSec（Ph）），并将其用于固相肽合成（SPPS）。一旦掺入肽中，苯硒化物官能团为通过氧化消除将E-或Z-脱氢丁酸残基位点和立体定向引入肽链提供了有用的处理。氧化条件温和，可以在固体支持物上进行，并且可以耐受肽中常见的功能，包括各种受保护的半胱氨酸残基。含有未保护的半胱氨酸残基的脱氢肽经过分子内立体选择性缀合物加成，得到环状羊毛硫氨酸和甲基羊毛硫氨酸，具有与羊毛硫抗生素相同的立体化学，羊毛硫抗生素是核糖体合成和翻译后修饰的肽抗生素家族。已显示观察到的立体选择性源自动力学而不是热力学偏好。
• Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry
  作者：Yasuhiro Meguro、Masato Noguchi、Gefei Li、Shin-ichiro Shoda

  DOI：10.1021/acs.orglett.7b03400

  日期：2018.1.5

  thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named “glycosyl Bunte salts” after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water–acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation

  S-糖基硫代硫酸盐已被发现是糖化学中的一类新型合成中间体，以19世纪德国化学家汉斯·邦特（Hans Bunte）的名字命名为“糖基邦特盐”。通过在水-乙腈混合溶剂中使用甲am型脱水剂将未保护的糖和硫代硫酸钠直接缩合来完成合成。通过向其他糖基化合物如1-硫糖，糖基二硫化物，1，6-脱水糖和O-糖苷的转化反应证明了糖基邦特盐的应用。
• Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates
  作者：Antony J. Fairbanks

  DOI：10.1016/j.carres.2020.108197

  日期：2021.1

  its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations

  2-氯-1,3-二甲基咪唑啉氯化物（DMC，本文也称为 Shoda 试剂）及其衍生物可用于许多合成转化，其中未保护的还原糖的异头中心在水溶液中被选择性激活。由于此类未受保护的糖可以用一系列添加的亲核试剂进行异头取代，从而为一系列糖苷和糖缀合物提供高效途径，而无需进行传统的保护基操作。这篇简短的评论总结了 DMC 及其一些衍生物/类似物的发展，并重点介绍了保护无基团合成的最新应用。