methyl 4,6-O-benzylidene-2-O-Cbz-α-D-glucopyranoside | 320590-94-1

• 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: methyl 4,6-O-benzylidene-2-O-Cbz-α-D-glucopyranoside
• 英文别名: methyl 2-O-benzyloxycarbonyl-4,6-O-benzylidene-α-D-glucopyranoside；[(2R,4aR,6S,7R,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzyl carbonate
• CAS: 320590-94-1
• 化学式: C₂₂H₂₄O₈
• 分子量: 416.428
• InChiKey: SDUWPJULVNUPGU-RLLAOZKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2-O-Cbz-α-D-glucopyranoside 在 钯 氢气 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 methyl 3-O-myristoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Yoshimoto, Kimihiro; Itatani, Yoshitaka; Shibata, Kanoko, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 208 - 219

  摘要：

  DOI：
• 作为产物：
  描述：

  氯甲酸苄酯 、 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以89%的产率得到methyl 4,6-O-benzylidene-2-O-Cbz-α-D-glucopyranoside
  参考文献：
  名称：

  氯化亚锡是一种低毒且非常廉价的催化剂，用于区域/部位选择性酰化反应，具有异常广泛的底物范围

  摘要：

  这项工作报告了氯化亚锡（SnCl 2）催化的区域/位点选择性酰化反应，其底物范围异常广泛。除了含有顺式-邻位二醇的1,2-和1,3-二醇和糖苷外，底物范围还包括不含顺式-邻位二醇的糖苷。对于这种底物范围，通常，只有使用化学计量的有机锡试剂的方法才能以高选择性和高分离产率（大多数情况下为84–97％）产生相同的保护模式。因此，与以前报道的任何试剂相比，SnCl 2作为一种低毒且极其便宜的试剂，应该是区域/位点选择性酰化反应的最佳催化剂。

  DOI：

  10.1039/d0gc02739a

文献信息

• Preparation of trifluoroethyl- and phenyl-protected sulfates using sulfuryl imidazolium salts
  作者：Ahmed Y. Desoky、Jennifer Hendel、Laura Ingram、Scott Douglas Taylor

  DOI：10.1016/j.tet.2010.11.085

  日期：2011.2

  Sulfuryl imidazolium salts (SIS's), a new class of sulfating agents, were prepared bearing the trifluoroethyl (TFE) and phenyl groups, two functionalities that have been used for the protection of sulfate monoesters, by subjecting the corresponding sulfonyl imidazoles with methyl triflate. In contrast, SIS's bearing the electron donating neopentyl and isobutyl groups, two moieties that have also been used for the protection of sulfates, were found to be unstable and could not be isolated though SIS's bearing electron donating aryl groups, such as a p-methoxyphenyl or p-thiomethylphenyl group were readily prepared and are stable compounds. In most instances, TFE-protected phenolic and carbohydrate sulfates were obtained in good yield by reaction of the corresponding SIS's with steroids and carbohydrates. Phenyl-protected carbohydrates were also readily prepared using the corresponding SIS's. Those SIS's having a methyl group at the 2-position of the imidazole ring were, in general, superior sulfating agents to those, which lacked a methyl group at this position. The use of SIS's to prepare TFE-protected sulfates represents a significant improvement of the previous reported procedure, which involved treating unprotected sulfates with trifluorodiazoethane. The TFE protecting group was removed from steroidal sulfates and secondary sulfates in carbohydrates in high yields using NaN(3) in warm DMF, conditions that are less vigorous than those previously reported for removing this group. Deprotection of TFE-protected 6-sulfated carbohydrates using NaN3 in warm DMF proceeded in lower yields due to partial desulfation. (C) 2010 Elsevier Ltd. All rights reserved.
• An easy and efficient approach for the installation of alkoxycarbonyl protecting groups on carbohydrate hydroxyls
  作者：Matteo Adinolfi、Gaspare Barone、Luigi Guariniello、Alfonso Iadonisi

  DOI：10.1016/s0040-4039(00)01673-7

  日期：2000.11

  Alkoxycarbonyl groups can be readily installed on carbohydrates by reaction with the corresponding chloroformates in the presence of TMEDA at low temperature. The mild reaction conditions can be modulated to attain regioselective protections. (C) 2000 Elsevier Science Ltd. Ail rights reserved.
• Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope
  作者：Jian Lv、Jian-Cheng Yu、Guang-Jing Feng、Tao Luo、Hai Dong

  DOI：10.1039/d0gc02739a

  日期：——

  containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84–97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst

  这项工作报告了氯化亚锡（SnCl 2）催化的区域/位点选择性酰化反应，其底物范围异常广泛。除了含有顺式-邻位二醇的1,2-和1,3-二醇和糖苷外，底物范围还包括不含顺式-邻位二醇的糖苷。对于这种底物范围，通常，只有使用化学计量的有机锡试剂的方法才能以高选择性和高分离产率（大多数情况下为84–97％）产生相同的保护模式。因此，与以前报道的任何试剂相比，SnCl 2作为一种低毒且极其便宜的试剂，应该是区域/位点选择性酰化反应的最佳催化剂。
• Yoshimoto, Kimihiro; Itatani, Yoshitaka; Shibata, Kanoko, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 208 - 219
  作者：Yoshimoto, Kimihiro、Itatani, Yoshitaka、Shibata, Kanoko、Tsuda, Yoshisuke

  DOI：——

  日期：——