thexyldimethylsilyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranoside | 160720-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thexyldimethylsilyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranoside
• 英文别名: thexyldimethylsilyl 2a-azido-2a-deoxy-3b,4b-O-isopropylidene-lactoside；(3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-azido-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 160720-72-9
• 化学式: C₂₃H₄₃N₃O₁₀Si
• 分子量: 549.694
• InChiKey: KPZFACDIEAAWDL-BNPIJXQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  thexyldimethylsilyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranoside 在 吡啶 、 zinc chloride diethyl ether 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(3aS,4R,6S,7R,7aS)-6-[(2R,3S,4R,5R)-4-acetyloxy-5-azido-2-(benzoyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-7-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-methyl-3-phenylmethoxyoxan-2-yl]oxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
  参考文献：
  名称：

  内酯系列抗原H，Lewis X（Le x）和Lewis Y（Le y）1的高效合成

  摘要：

  叠氮半乳糖4的区域选择性61,6b-二-O-苯甲酰化提供了衍生物6，其允许随后进行区域选择性2b-O-岩藻糖基化，2b，3a-di-O-岩藻糖基化或区域选择性2b-O-苯甲酰化，然后是3a-O-岩藻糖基化分别直接提供H，Le y和Le x抗原构件8a-c。衍生的三氯乙酰亚氨酸酯9a-c提供了部分受O保护的受体5和13的区域和β-选择性糖基化，提供了间隔连接的H，Le x，Le y，二聚体Le x和Le y中间体12a-c可以分别容易地转化成目标分子1a-c和2b，c以及14b ，c。因此，显示了该抗原系列的最直接和最有效的合成。

  DOI：

  10.1016/0040-4039(94)80013-8
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-5-azido-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-4-yl ester 在 三氟甲磺酸三甲基硅酯 、 Sikkon 、 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.92h， 生成 thexyldimethylsilyl 3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of building blocks of human milk oligosaccharides. Fucosylated derivatives of the lacto- and neolacto-series

  摘要：

  The synthesis of protected fucosylated derivatives of a Gal beta(1--> 3)GlcNAc and of lactosamine Galbeta(1--> 4)GlcNAc building blocks contained in human milk oligosaccharides is described. Both chemical and enzymatic methods have been exploited for selective protection of the disaccharide. Fucosylation of the appropriate derivatives allowed an easy and relatively short access to different products from common precursors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00164-7

文献信息

• Synthesis of building blocks of human milk oligosaccharides. Fucosylated derivatives of the lacto- and neolacto-series
  作者：Barbara La Ferla、Davide Prosperi、Luigi Lay、Giovanni Russo、Luigi Panza

  DOI：10.1016/s0008-6215(02)00164-7

  日期：2002.9

  The synthesis of protected fucosylated derivatives of a Gal beta(1--> 3)GlcNAc and of lactosamine Galbeta(1--> 4)GlcNAc building blocks contained in human milk oligosaccharides is described. Both chemical and enzymatic methods have been exploited for selective protection of the disaccharide. Fucosylation of the appropriate derivatives allowed an easy and relatively short access to different products from common precursors. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Efficient synthesis of lactoneo series antigens H, Lewis X (Lex), and Lewis Y (Ley)1
  作者：Rainer Windmüller、Richard R. Schmidt

  DOI：10.1016/0040-4039(94)80013-8

  日期：1994.10

  directly H, Ley, and Lex antigen building blocks 8a-c. The derived trichloroacetimidates 9a-c offered regio- and β-selective glycosylations of partially O-protected acceptors 5 and 13, affording spacer-linked H, Lex, Ley, dimer Lex and Ley intermediates 12a-c and 14b,c, respectively, which could be readily transformed into target molecules 1a-c and 2b,c. Thus, a most straightforward and efficient synthesis

  叠氮半乳糖4的区域选择性61,6b-二-O-苯甲酰化提供了衍生物6，其允许随后进行区域选择性2b-O-岩藻糖基化，2b，3a-di-O-岩藻糖基化或区域选择性2b-O-苯甲酰化，然后是3a-O-岩藻糖基化分别直接提供H，Le y和Le x抗原构件8a-c。衍生的三氯乙酰亚氨酸酯9a-c提供了部分受O保护的受体5和13的区域和β-选择性糖基化，提供了间隔连接的H，Le x，Le y，二聚体Le x和Le y中间体12a-c可以分别容易地转化成目标分子1a-c和2b，c以及14b ，c。因此，显示了该抗原系列的最直接和最有效的合成。