(1'R,1R,2E)-benzoic acid 1-(1'-azido-2'-hydroxyethyl)hexadec-2-enyl ester | 152142-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1'R,1R,2E)-benzoic acid 1-(1'-azido-2'-hydroxyethyl)hexadec-2-enyl ester
• 英文别名: (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadencene-1,3-diol；(2S,3R,4E)-2-Azido-3-O-benzoyl-4-octadecene-1,3-diol；(2S,3R,4E)-2-azido-3-benzoyloxy-octadec-4-ene-1-ol；[(E,2R,3R)-2-azido-1-hydroxyoctadec-4-en-3-yl] benzoate
• CAS: 152142-06-8
• 化学式: C₂₅H₃₉N₃O₃
• 分子量: 429.603
• InChiKey: ORUYONFWESLTQS-QIOSQNANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  31.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.29
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1'R,1R,2E)-benzoic acid 1-(1'-azido-2'-hydroxyethyl)hexadec-2-enyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.5h， 生成
  参考文献：
  名称：

  [EN] THE PREPARATION OF CERAMIDE CONJUGATES AND DERIVATIVES OF SPHINGOLIPID ANALOGUES
  [FR] PRÉPARATION DE CONJUGUÉS DE CÉRAMIDES ET DE DÉRIVÉS D'ANALOGUES DE SPHINGOLIPIDES

  摘要：

  描述了水分散型酯化物和鞘脂类似物衍生物的制备。这些酯化物和类似物是通过将β-丙氨酸衍生物的琥珀酰亚胺碳酸酯与功能化间隔物的主要胺基反应制备的。尽管它们在水中可分散，但酯化物和鞘脂类似物衍生物会自发地纳入细胞的质膜中。

  公开号：

  WO2018220603A1
• 作为产物：
  描述：

  (2R,3R,4E)-2-azido-octadec-4-ene-1,3-diol 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1'R,1R,2E)-benzoic acid 1-(1'-azido-2'-hydroxyethyl)hexadec-2-enyl ester
  参考文献：
  名称：

  Synthesis of fluorescent lactosylceramide stereoisomers

  摘要：

  The intracellular distribution of synthetic glycosphingolipids (GSLs) bearing a fluorophore can be monitored in living cells by fluorescence microscopy. We reported previously that variation in the length of the long-chain base and in the structure of the carbohydrate-containing polar head group of (2S,3R) (or D-erythro-)-beta-lactosylceramide (LacCer) did not alter the mechanism of endocytic uptake from the plasma membrane of various mammalian cell types [Singh, R.D., Puri, V., Valiyaveettil, J.T., Marks, D.L., Bittman, R., Pagano, R.E., 2003. Selective caveolin-l-dependent endocytosis of glycosphingolipids. Mol. Biol. Cell 14, 3254-3265]. To extend our examination of the molecular features in LacCer that are responsible for its uptake by the caveolar-requiring endocytic pathway, we have synthesized the three unnatural stereoisomers [(2R,3R)-, (2S,3S)-, and (2R,3S)] of dipyrromethene difluoride (BODIPY (TM))-LacCer. These analogues will be used to probe the role of stereochemistry in the long-chain base of LacCer in the mechanism of endocytic uptake. (c) 2006 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2006.03.001

文献信息

• Synthesis of a position isomer of ganglioside GD3having an α-Neu5Ac-(2→9)-α-Neu5Ac linkage
  作者：Akira Hasegawa、Hirotsugu Ogawa、Makoto Kiso

  DOI：10.1016/0008-6215(92)84104-z

  日期：1992.2

  3 structure. The coupling of 2-(trimethylsilyl)ethyl O -(6- O -benzoyl-β- d -galactopyranosyl)-(1→4)-2,6-di- O -benzoyl-β- d -glucopyranoside with methyl O -(methyl 5-acetamido-4,7,8,9-tetra- O -acetyl-3,5-dideoxy- d - glycero -α- d - galacto -2-nonulopyranosylonate)-(2→ 9)-(methyl 5-acetamido-4,7,8-tri- O -acetyl-3,5-dideoxy-2-thio- d - glycero - d - galacto -2-nonulopyranosid)onate, prepared from

  摘要合成了神经节苷脂GD 3的位置异构体，其中N-乙酰神经氨酸（Neu5Ac）在神经节苷脂GM 3结构的Neu5Ac残基的C-9处以α-糖苷键连接。2-（三甲基甲硅烷基）乙基O-（6-O-苯甲酰基-β-d-吡喃半乳糖基）-（1→4）-2,6-二-O-苯甲酰基-β-d-吡喃葡萄糖苷与甲基O-的偶联（5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-d-甘油-α-d-半乳糖-2-壬基吡喃二磺酸酯）-（2→9）-（甲基5 -乙酰氨基-4,7,8-三-O-乙酰基-3,5-二脱氧-2-硫代-d-甘油-d-半乳糖-2-壬基吡喃二酮基）酸酯，由相应的2-（三甲基甲硅烷基）乙基糖苷制得通过选择性除去2-（三甲基甲硅烷基）乙基，进行1-O-乙酰化，并通过三甲基（甲硫基）硅烷引入甲硫基，用N-碘琥珀酰亚胺-三氟甲磺酸作为糖基化催化剂，得到四糖（5）。化合物5通过O-乙酰化，选择性除去2-（三甲基甲
• Synthesis of an S-(α-sialosyl)-(2→9)-O-(α-sialosyl)-(2→3′)-β-lactosylceramide
  作者：Akira Hasegawa、Hirotsugu Ogawa、Hideharu Ishida、Makoto Kiso

  DOI：10.1016/0008-6215(92)84103-y

  日期：1992.2

  Neu5Ac residue in the ganglioside GM3 structure. Glycosylation of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-beta-D-galactopyranosyl)-(1----4)-2,6-di-O-benzoyl-beta-D -glucopyranoside with methyl (methyl 5-acetamido-4,7,8-tri-O-acetyl-9-bromo-3,5,9-trideoxy-D-glycero-alpha-D- galacto-2-nonulopyranosid)onate, which was prepared from methyl (methyl 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2- nonulopyranosid)onate

  已经合成了神经节苷脂GD3类似物，其具有与神经节苷脂GM3结构中的Neu5Ac残基的C-9连接的N-乙酰神经氨酸（Neu5Ac）残基α-硫糖苷。O-（6-O-苯甲酰基-β-D-吡喃半乳糖基）-（1 ---- 4）-2,6-二-O-苯甲酰基-β-D-吡喃葡萄糖苷的2-（三甲基甲硅烷基）乙基糖基与甲基（5-5-乙酰氨基-4,7,8-三-O-乙酰基-9-溴-3,5,9-苯氧基氧基-D-甘油-α-D-半乳糖-2-壬基吡喃糖苷） （8,9-O-异丙基亚甲基化，O-乙酰化，异亚丙基基团的水解，选择性溴化，5-乙酰氨基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬基吡喃甲基）甲基酸酯然后使用三氟甲磺酸二甲基（甲硫基）ulf（DMTST）作为促进剂进行O-乙酰化反应，得到α-唾液酰-（2 ---- 3'）-乳糖苷8。8的O-乙酰基衍生物与5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-2
• A short and practical route to 3-O-benzoyl azidosphingosine
  作者：Jörgen Ohlsson、Göran Magnusson

  DOI：10.1016/s0008-6215(00)00323-2

  日期：2001.3

  A short and practical route to 3-O-benzoyl azidosphingosine from D-xylose is described. The synthesis avoids the use of expensive and hazardous chemicals (i.e. mercury salts), and it is reproducible up to at least a 20 g scale. Furthermore, the synthesis proceeds to 3-O-benzoyl azidosphingosine with a minimum of protection group manipulation, by exploiting a regioselective protection of the primary

  描述了从D-木糖制备3-O-苯甲酰基叠氮鞘氨醇的短而实用的途径。合成过程避免使用昂贵和危险的化学药品（例如汞盐），并且可重现至少20 g的规模。此外，通过利用伯基二甲基甲硅烷基氯对伯HO-1进行区域选择性保护，合成以最少的保护基团操作进行到3-O-苯甲酰基叠氮基鞘氨醇。
• Versatile approach to the synthesis of globoside glycosphingolipids synthesis of sialyl-galactosyl-globoside
  作者：JoséM. Lassaletta、Richard R. Schmidt

  DOI：10.1016/0040-4039(95)00771-4

  日期：1995.6

  Sialyl-galactosyl-globoside (SGG, 1), carrying the SSEA-4 antigen, is synthesized from readily available, versatile building blocks 2–;7 in a convergent manner. Thus, appropriately protected tetra- and pentasaccharides 15 and 17 are generated, which constitute valuable intermediates for the synthesis of various other members of the globo-series of glycosphingolipids.

  带有SSEA-4抗原的唾液酸-半乳糖基-球蛋白苷（SGG，1）是由容易获得的，通用的构建基块2 ;; 7以聚合方式合成的。因此，适当保护的四-和五糖15和17中产生，这构成用于各种其他成员的合成有价值的中间体的Globo鞘糖脂的-SEries。
• Synthetic Studies on Sialoglycoconjugates 85: Synthesis of Sialyl Lewis X Ganglioside Analogs Containing a Variety of Anionic Substituents in Place of Sialic Acid
  作者：Masahiro Yoshida、Yukiko Kawakami、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1080/07328309608005662

  日期：1996.5

  Three sialyl-Le(X) ganglioside analogs containing carboxymethyl, sulfate, and phosphate groups in place of the sialic acid moiety, have been synthesized. Glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,3-tri-O-benzyl-alpha-L-fucopyranosyl)-(1 --> 3) -O- (2-acetamido-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl) - (1 --> 3) - 2,4,6-tri-O-benzyl-beta-D-galactopyranoside (10) with methyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-1-thio-beta-D-galactopyranoside (6) or methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-beta-D-galactopyranoside (9) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding tetrasaccharide derivatives 11 and 19. Compounds 11 and 19 were converted into the alpha-trichloroacetimidates 14 and 23, via reductive removal of the benzyl and benzylidene groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (15) or 2-(tetradecyl)hexadecan-1-ol (24), gave the lipophilic derivatives 16 and 25. Compound 16 was transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title compound 18 in good yield. Compound 25 was treated with hydrazine acetate to give compound 26, which in turn was transformed, via sulfation or phosphorylation, and O-deacylation, into the target compounds 28 and 31.