2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 128716-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: GlcNAc(b1-3)[Bn(-2)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-EtTMS；N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 128716-23-4
• 化学式: C₆₇H₈₃NO₁₆Si
• 分子量: 1186.48
• InChiKey: FAEXNVMVXZKFNY-NBRUXRFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.28
• 重原子数：
  85
• 可旋转键数：
  30
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 对甲苯磺酸 作用下， 以83%的产率得到2-(trimethylsilyl)ethyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  唾液酸乳四糖基神经酰胺的全合成

  摘要：

  滴定合成部分d'O-β-D-吡喃半乳糖基-4 O-三甲基甲硅烷基-2'乙基-1吡喃葡萄糖苷等和脱氧2邻苯二甲酰亚胺2三-O-乙酰基-3,4,6吡喃葡萄糖苷等N-乙酰基O- [O-苯甲酰基-6 O-三甲基甲硅烷基-2'乙基-1β-D-吡喃半乳糖苷基-3] -2神经氨基酸酯

  DOI：

  10.1016/0008-6215(89)85136-5
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 在 molecular sieve 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Neolactotetraose Glycoside Suitable for Enzymatic Elaboration to the Sialyl Lewis X Stage

  摘要：

  A tetrasaccharide glycoside comprising the core of the sialyl Lewis X structure was synthesized from "building-block" derivatives of the component sugar units. Initially 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2',1':4,5]-2-oxazoline (1) was coupled to the known 2-(trimethylsilyl) ethyl 2,3,6,2',4',6'-hexa-O-benzyl-beta-D-lactoside to give a trisaccharide glycoside (3) in 60% yield. De-O-acetylation, benzylidenation, benzylation, and reductive opening of the benzylidene acetal function of 6 gave a derivative having OH-4" open. This derivative was coupled with tetra-O-acetyl-alpha-D-galactosyl bromide to give a tetrasaccharide in 62% yield, and the product was de-O-acetylated and de-O-benzylated to give the target compound, 2-(trimethylsilyl)ethyl beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranoside (11).

  DOI：

  10.1080/07328309808002327

文献信息

• First total synthesis of α-(2→3)/α-(2→6)-disialyl lactotetraosyl ceramide and disialyl Lewis A ganglioside as cancer-associated carbohydrate antigens
  作者：Takayuki Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.1016/s0008-6215(02)00465-2

  日期：2003.3

  Abstract The first total synthesis of α-(2→3)/α-(2→6)-disialyl lactotetraosyl (DSLc 4 ) ceramide and α-(2→3)/α-(2→6)-disialyl Lewis A (DSLe a ) ganglioside as cancer-associated antigens is described. The suitably protected lactotriose (Lc 3 ) derivatives were successively glycosylated with sialic acid, sialyl-α-(2→3)- d -galactose and/or l -fucose donors in a regio- and stereo-selective manner, to

  摘要α-（2→3）/α-（2→6）-二唾液酸乳糖四糖基（DSLc 4）神经酰胺和α-（2→3）/α-（2→6）-二唾液酸Lewis A（描述了DSLe a）神经节苷脂作为癌症相关抗原。将适当保护的乳三糖（Lc 3）衍生物以区域和立体选择性方式依次用唾液酸，唾液酸-α-（2→3）-d-半乳糖和/或1-岩藻糖供体糖基化，得到被保护的I型六糖和七糖分别通过引入神经酰胺和随后的完全脱保护作用分别转化为目标神经节苷脂。
• Stereoselective synthesis of sialyl-lactotetraosylceramide and sialylneolactotetraosylceramide
  作者：Akihiko Kameyama、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/0008-6215(90)84197-3

  日期：1990.4

  3)-6-O-benzoyl-beta-D-galactopyranosid e (1), via benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with methylthiotrimethylsilane. Coupling of 2-(trimethylsilyl) ethyl 2,3,6,2',4',6'-hexa-O-benzyl-beta-D-lactoside (8), prepared from 2-(trimethylsilyl)ethyl beta-D-lactoside (5) via selective 3'-O-(4-methoxybenzylation), benzylation, and

  描述了唾液酸基-乳基四糖基神经酰胺（28，IV3NeuAcLc4Cer）和唾液酸基神经元四糖基神经酰胺（32，IV3NeuAcnLc4Cer）的第一全部合成。O-（5-乙酰氨基甲基-4,7,8,9-四-O-乙酰基-3,5-二甲氧基-D-甘油-α-D-半乳糖-2-壬基吡喃二磺酸甲酯）-（2 ---- 3）-2,4,6-三-O-苯甲酰基-1-硫代-β-D-吡喃半乳糖苷（4）是关键的糖基供体，由2-（三甲基甲硅烷基）乙基O-（甲基5-乙酰氨基）制得-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬基吡喃二磺酸根）-（2 ---- 3）-6-O-苯甲酰基-β-D-吡喃半乳糖苷（1），通过苯甲酰化，用乙酰基取代2-（三甲基甲硅烷基）乙基，并用甲硫基三甲基硅烷引入甲硫基。2-（三甲基甲硅烷基）乙基2,3,6,2'，4'，6'-六-O-苄基-β-D-乳糖苷（8）的偶联，由
• Synthesis of Sialyl-α-(2→3)-Neolactotetraose Derivatives Containing Different Sialic Acids: Molecular Probes for Elucidation of Substrate Specificity of Human α1,3-Fucosyltransferases
  作者：Eiji Tanahashi、Kyoko Fukunaga、Yuko Ozawa、Tsuyoshi Toyoda、Hidcharu Ishida、Makoto Kiso

  DOI：10.1080/07328300008544114

  日期：2000.1

  A series of sialyl-alpha-(2-->3)-neolactotetraose derivatives containing N-acetyl-(NeuAc), N-glycolyl- (NeuGc) and N-butanoylneuraminic acid, and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) have systematically been synthesized as molecular probes for elucidation of substrate specificity of human alpha 1,3-fucosyltransferases (Fuc-TVII and Fuc-TVI). 2-Methyl-(3,4, 6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopylano)-[2',1' :4,5]-2-oxazoline (1) was coupled with 2-(trimethyl-silyl)-ethyl (2,4,6-tri-O-benzyl-beta-D-galactopyranosyl) -(1 --> 4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside (2) to give a trisaccharide 3 which, upon successive O-deacetylation, benzylidenation and reductive opening of the benzylidene group, afforded a common glycosyl acceptor 5. Glycosylation of 5 with sialyl-alpha-(2-->3)-galactose donors 6-8, 19 and 21 gave the corresponding pentasaccharides 22-25, which were converted to a series of sialyl-alpha-(2-->3)-neolactotetraose derivatives 30-33. In the competitive enzyme assay, the NeuGc derivative 32 showed the most potent activity for Fuc-TVII, while the KDN derivative 31 was less active than the standard NeuAc derivative 30. In contrast, the N-butanoylation of neuraminic acid enhanced the activity for Fuc-TVI.
• KAMEYAMA, AKIHIKO;ISHIDA, HIDEHARU;KISO, MAKOTO;HASEGAWA, AKIRA, CARBOHYDR. RES., 193,(1989) C1-C5
  作者：KAMEYAMA, AKIHIKO、ISHIDA, HIDEHARU、KISO, MAKOTO、HASEGAWA, AKIRA

  DOI：——

  日期：——