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2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate | 4196-36-5

中文名称
——
中文别名
——
英文名称
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate
英文别名
alpha-D-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylmethyl)-, 1-(4-nitrobenzoate);[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 4-nitrobenzoate
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate化学式
CAS
4196-36-5
化学式
C41H39NO9
mdl
——
分子量
689.762
InChiKey
IJTANGJQVDVKFH-ZWWYPIQLSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    125.0-126.5 °C
  • 沸点:
    793.7±60.0 °C(Predicted)
  • 密度:
    1.29±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    7
  • 重原子数:
    51
  • 可旋转键数:
    16
  • 环数:
    6.0
  • sp3杂化的碳原子比例:
    0.24
  • 拓扑面积:
    118
  • 氢给体数:
    0
  • 氢受体数:
    9

SDS

SDS:0d2e763f920b656d9d4ae6f0ac5a069a
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    含有油酰基磷脂酰部分的磷脂酰-α-葡萄糖基甘油的合成。四异丙基二硅氧烷-1,3-二基(尖端)保护基在糖化学中的应用。第三部分1
    摘要:
    在这项研究中,我们证明了可以通过两步操作在α-葡萄糖基甘油二酸酯3的3'-和4'-羟基官能团处引入四异丙基二硅氧烷-1,3-二基保护基团以生成衍生物6。化合物6可以可以在其伯羟基官能团上与适当保护的磷脂酰部分9选择性缩合,得到保护的糖磷脂10a。磷脂酰部分9是通过将光学纯的1,2-二-O-油酰基-sn-甘油(8a)用磷酸二三唑酯7b磷酸化而获得的。最后,分别通过顺-4-硝基苯甲酰肟酸酯和氟离子从10a中除去2,4-二氯苯基和TIPS保护基,得到糖脂10c。
    DOI:
    10.1016/s0040-4020(01)82349-8
  • 作为产物:
    参考文献:
    名称:
    Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors
    摘要:
    Biomimetic conditions for a synthetic glycosylation reaction, inspired by the highly conserved functionality of carbohydrate active enzymes, were explored. At the outset, we sought to generate proof of principle for this approach to developing catalytic systems for glycosylation. However, control reactions and subsequent kinetic studies showed that a stoichiometric, irreversible reaction of the catalyst and glycosyl donor was occurring, with a remarkable rate variance depending upon the structure of the carboxylic acid. It was subsequently found that a combination of Bronsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the desired transformation. The role of the catalytic components was tested with a number of control reactions and based on these studies a mechanism is proposed herein. (C) 2013 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.carres.2013.09.011
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文献信息

  • Phosphotriester approach to the synthesis of α-glucosylated mono- and diphosphatidyl glycerols: bacterial cell-wall components
    作者:C.A.A. van Boeckel、J.J. Oltvoort、Jh. van Boom
    DOI:10.1016/s0040-4020(01)98907-0
    日期:1981.1
    phosphorylating agents, 2,2,2-tribromoethyl and 2-chlorophenyl phosphorodichloridate, were used with 1,2,4-triazole to assemble phosphotriester derivatives of protected α-glucosyl mono- and diphosphatidyl glycerols. Benzyl, allyl and pivaloyl groups were used for the protection of the hydroxyl functions of the glucose and glycerol moieties, respectively. The merits of the pivaloyl group are discussed. Finally
    两种双功能磷酸化剂2,2,2-三乙基和2-氯苯基二磷酸酯与1,2,4-三唑一起使用,以组装受保护的α-葡萄糖基单和二磷脂甘油磷酸三酯衍生物。苄基,烯丙基和新戊酰基分别用于保护葡萄糖甘油部分的羟基功能。讨论了新戊酰基的优点。最后,要特别注意将磷酸三酯转化为所需的磷酸二酯功能。
  • Synthesis of Chiral Spiroacetals from Carbohydrates
    作者:Angeles Martín、José A. Salazar、Ernesto Suárez
    DOI:10.1021/jo960060g
    日期:1996.1.1
    Chiral spiroacetals of the 1,7-dioxaspiro[5.5]undecane, 1,6-dioxaspiro[4.5]decane, and 1,6-dioxaspiro[4.4]nonane types have been prepared from carbohydrates in pyranose or furanose forms. The spirocyclization reaction has been accomplished from a conveniently homologated carbohydrate by an intramolecular hydrogen abstraction reaction promoted by alkoxy radicals. Thus, 2,3,4,6-tetra-O-benzyl-1-deox
    喃糖或呋喃糖形式的碳水化合物制备了1,7-二氧杂螺[5.5]十一烷,1,6-二氧杂螺[4.5]癸烷1,6-二氧杂螺[4.4]壬烷类型的手性螺缩醛。螺环化反应已经通过由烷氧基自由基促进的分子内氢提取反应,从便利地同源的碳水化合物完成。因此,在(二乙酰氧基)苯存在下,用可见光光解2,3,4,6-四-O-苄基-1-脱氧-1-(3'-羟丙基)-α-D-吡喃葡萄糖(2)。和制得(1R)-(3)和(1S)-2,3,4,6-四-O-苄基-1-脱氧-D-吡喃葡萄糖-1-螺-2'-四氢呋喃的混合物( 4)。甲基6-脱氧-6-(2'-羟乙基)-2,3,4-三-O-甲基-α-D-吡喃葡萄糖苷(8)的光解得到异构的螺缩醛甲基(5S)-(9)和(5R)-6-脱氧-5,2'-环氧-6-乙基-2,3,4-螺-O-甲基-α-D-吡喃葡萄糖苷(10)的螺中心现在位于C-5。[5.5]十一烷系列的螺缩醛:甲基(5R)-(19)和(5S)-6-脱氧-5
  • Syntheses of 1-O-acylaldose derivatives via the corresponding O-glycosylpseudoureas
    作者:Hideo Tsutsumi、Yoshiharu Ishido
    DOI:10.1016/0008-6215(82)85008-8
    日期:1982.12
    Abstract A series of 1- O -acylaldose derivatives was prepared in good yield through the reaction of 1,3-dialkyl- O -glycosylpseudoureas with carboxylic acids.
    摘要通过1,3-二烷基-O-糖基假单胞菌与羧酸的反应,高收率地制备了一系列1-O-酰基醛糖衍生物
  • A Novel Glycosidation Promoted by the Combination of Trimethylsilyl Halide and Zinc Triflate.
    作者:Kunio HIGASHI、Hiroshi SUSAKI
    DOI:10.1248/cpb.40.2019
    日期:——
    A novel glycosidation method has been developed which utilizes a trimethylsilyl halide-zinc triflate catalyst system to activate various benzyl-protected fucosyl, glucosyl and galactosyl esters. The promoter system was extended to use benzyl-protected alkyl glycosides and N-2, 2, 2, -trichloroethoxycarbonyl-protected glucosaminyl and galactosaminyl acetates as glycosyl donors.
    我们开发了一种新型糖苷化方法,它利用三甲基卤化物-三late催化剂体系来激活各种苄基保护的岩藻糖基、葡萄糖基和半乳糖基酯。该促进剂体系已扩展到使用苄基保护的烷基糖苷和 N-2,2,2,-三乙氧羰基保护的葡萄糖酰和半乳糖醋酸盐作为糖基供体。
  • Preparative synthesis of C-(α-d-glucopyranosyl)-alkenes and -alkadienes: Diels-alder reaction
    作者:Maria de Gracia Garcia Martin、Derek Horton
    DOI:10.1016/0008-6215(89)85066-9
    日期:1989.8
    The reaction of 2,3,4,6-tetra-O-benzyl-1-O-(p-nitrobenzoyl)-alpha-D-glucopyranose with (E)-penta-2,4-dienyltrimethylsilane and boron trifluoride etherate in acetonitrile afforded stereoselectively (E)-5-(tetra-O-benzyl-alpha-D-glucopyranosyl)-1,3-pentadiene in good yield. The readily available penta-O-benzoyl-alpha-D-glucopyranose reacted with allyltrimethylsilane in the presence of boron trifluoride
    2,3,4,6-四-O-苄基-1-O-(对硝基苯甲酰基)-α-D-吡喃葡萄糖与(E)-戊-2,4-二烯基三甲基硅烷三氟化硼醚化物在乙腈中的反应以良好的收率得到立体选择性地(E)-5-(四-O-苄基-α-D-吡喃葡萄糖基)-1,3-戊二烯。在乙腈中,在三氟化硼醚化物的存在下,易于获得的五-O-苯甲酰基-α-D-吡喃葡萄糖与烯丙基三甲基硅烷反应,生成3-(四-O-苯甲酰基-α-D-吡喃葡萄糖基)-1-丙烯及其β异构体的产率分别为60%和2.3%。将马来酸酐的Diels-Alder环加成成二烯1可以高收率得到加成物顺式,顺式3-(四-O-苄基-α-D-吡喃葡萄糖基甲基)环己基-4-烯-1,2-二羧酸酐
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同类化合物

(βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S,S)-邻甲苯基-DIPAMP (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-盐酸沙丁胺醇 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(-)-4,12-双(二苯基膦基)[2.2]对环芳烷(1,5环辛二烯)铑(I)四氟硼酸盐 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(4-叔丁基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(3-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-4,7-双(3,5-二-叔丁基苯基)膦基-7“-[(吡啶-2-基甲基)氨基]-2,2”,3,3'-四氢1,1'-螺二茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-2-[((二苯基膦基)甲基]吡咯烷 (R)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4S,4''S)-2,2''-亚环戊基双[4,5-二氢-4-(苯甲基)恶唑] (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (3aR,6aS)-5-氧代六氢环戊基[c]吡咯-2(1H)-羧酸酯 (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[((1S,2S)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2-硝基苯基)磷酸三酰胺 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1S,2S,3R,5R)-2-(苄氧基)甲基-6-氧杂双环[3.1.0]己-3-醇 (1-(4-氟苯基)环丙基)甲胺盐酸盐 (1-(3-溴苯基)环丁基)甲胺盐酸盐 (1-(2-氯苯基)环丁基)甲胺盐酸盐 (1-(2-氟苯基)环丙基)甲胺盐酸盐 (1-(2,6-二氟苯基)环丙基)甲胺盐酸盐 (-)-去甲基西布曲明 龙蒿油 龙胆酸钠 龙胆酸叔丁酯 龙胆酸 龙胆紫-d6 龙胆紫