ethyl 4-O-trichloroacetimidoyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside | 146457-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl 4-O-trichloroacetimidoyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
• 英文别名: [(2R,3R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-ethoxy-3,6-dihydro-2H-pyran-3-yl] 2,2,2-trichloroethanimidate
• CAS: 146457-65-0
• 化学式: C₁₆H₂₈Cl₃NO₄Si
• 分子量: 432.847
• InChiKey: DDBDJKGEBACIPP-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-O-trichloroacetimidoyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 以 甲苯 为溶剂， 生成 ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-talopyranoside
  参考文献：
  名称：

  的2-氨基-2-脱氧合成d从4- -hexopyranosides ö -trichloroacetimidyl- d由[3,3] -sigmatropic重排-己-2-烯吡喃糖苷

  摘要：

  2-氨基-2-脱氧糖，d -mannosamine和d -altrosamine衍生物连同合成d -idosamine和d -talosamine那些从2-脱氧-2- trichloroacetamido -己-3-烯吡喃糖苷。该关键中间体是通过4 - O-三氯乙二酰亚胺-己-2-烯吡喃糖苷的区域和立体选择性[3,3]-σ重排而制备的。

  DOI：

  10.1016/s0040-4039(00)60858-4
• 作为产物：
  描述：

  ethyl 6-O-tert-butyldimethylsilyl-4-hydroxyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 甲醇 、 sodium methylate 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ethyl 4-O-trichloroacetimidoyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  的2-氨基-2-脱氧合成d从4- -hexopyranosides ö -trichloroacetimidyl- d由[3,3] -sigmatropic重排-己-2-烯吡喃糖苷

  摘要：

  2-氨基-2-脱氧糖，d -mannosamine和d -altrosamine衍生物连同合成d -idosamine和d -talosamine那些从2-脱氧-2- trichloroacetamido -己-3-烯吡喃糖苷。该关键中间体是通过4 - O-三氯乙二酰亚胺-己-2-烯吡喃糖苷的区域和立体选择性[3,3]-σ重排而制备的。

  DOI：

  10.1016/s0040-4039(00)60858-4

文献信息

• Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays
  作者：Ian Cumpstey、Jens Frigell、Elias Pershagen、Tashfeen Akhtar、Elena Moreno-Clavijo、Inmaculada Robina、Dominic S Alonzi、Terry D Butters

  DOI：10.3762/bjoc.7.128

  日期：——

  Diglycose derivatives, consisting of two monosaccharides linked at non-anomeric positions by a bridging nitrogen atom, have been synthesised. Conversion of one of the precursor monosaccharide coupling components into an unsaturated derivative enhances its electrophilicity at the allylic position, facilitating coupling reactions. Mitsunobu coupling between nosylamides and 2,3-unsaturated-4-alcohols gave the 4-amino-pseudodisaccharides with inversion of configuration as single regio- and diastereoisomers. A palladium-catalysed coupling between an amine and a 2,3-unsaturated 4-trichloroacetimidate gave a 2-amino-pseudodisaccharide as the major product, along with other minor products. Derivatisation of the C=C double bond in pseudodisaccharides allowed the formation of Man(N4–6)Glc and Man(N4–6)Man diglycosides. The amine-linked diglycosides were found to show weak glycosidase inhibitory activity.

  由两个单糖通过桥接氮原子在非异头位置连接而成的双糖衍生物已经合成出来。将其中一个前体单糖耦合组分转化为不饱和衍生物，增强了其在烯丙基位置的亲电性，从而促进了耦合反应。nosyl酰胺和2,3-不饱和-4-醇之间的Mitsunobu耦合得到了反转构型的4-氨基-假双糖，作为单一的区位和对映异构体。胺和2,3-不饱和的4-三氯乙酰亚胺之间的钯催化耦合得到了2-氨基-假双糖作为主要产物，同时还得到了其他次要产物。在假双糖中对C=C双键的衍生化允许形成Man(N4–6)Glc和Man(N4–6)Man双糖苷。发现胺连接的双糖苷显示出较弱的糖苷酶抑制活性。
• Synthesis of 2-amino-2-deoxy-D-hexopyranosides from 4-O-trichloroacetimidyl-D-hex-2-enopyranoside by [3,3]-sigmatropic rearrangement
  作者：Kazuyoshi Takeda、Eisuke Kaji、Yaeko Konda、Noriko Sato、Hiroko Nakamura、Noriko Miya、Aya Morizane、Yuko Yanagisawa、Akira Akiyama、Shonosuke Zen、Yoshihiro Harigaya

  DOI：10.1016/s0040-4039(00)60858-4

  日期：1992.11

  2-Amino-2-deoxysugars, D-mannosamine and D-altrosamine derivatives were synthesized together with D-idosamine and D-talosamine ones from a 2-deoxy-2-trichloroacetamido-hex-3-enopyranoside. This key intermediate was prepared by regio- and stereoselective [3,3]-sigmatropic rearrangement of 4-O-trichloroacetimidyl-hex-2-enopyranoside.

  2-氨基-2-脱氧糖，d -mannosamine和d -altrosamine衍生物连同合成d -idosamine和d -talosamine那些从2-脱氧-2- trichloroacetamido -己-3-烯吡喃糖苷。该关键中间体是通过4 - O-三氯乙二酰亚胺-己-2-烯吡喃糖苷的区域和立体选择性[3,3]-σ重排而制备的。