methyl 3-O-(2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranosyl)-β-D-galactopyranoside | 95795-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-(2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranosyl)-β-D-galactopyranoside
• 英文别名: methyl O-β-D-galactopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-β-galactopyranoside；methyl O-β-D-galactopyranosyl-(1<*>4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1<*>3)-β-D-galactopyranoside；Gal(b1-4)GlcNAc(b1-3)b-Gal1Me；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 95795-79-2
• 化学式: C₂₁H₃₇NO₁₆
• 分子量: 559.522
• InChiKey: NZJZIHWJSWDRGH-RFZGEEQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  267
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 3-O-(2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranosyl)-β-D-galactopyranoside 在 吡啶 作用下， 以87%的产率得到methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of methyl O-(2-O-methyl-β-d-galactopyranosyl)-(1 → 4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)- β-d-galactopyranoside and 4-nitrophenyl O-β-d-galactopyranosyl-(1 → 4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)-β-d-galactopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(90)80053-6
• 作为产物：
  描述：

  2-methyl{3,6-di-O-acetyl-1,2-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyrano}[2,1-d]oxazoline 在 palladium on activated charcoal 、 三氟甲磺酸三甲基硅酯 氢气 、 sodium methylate 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 41.0h， 生成 methyl 3-O-(2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  对应于肺炎链球菌识别的受体结构的二糖，三糖和四糖的合成

  摘要：

  摘要描述了甲基2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖苷-α-d-吡喃葡萄糖苷，甲基2-乙酰氨基-2-脱氧-4- O-β-d-吡喃半乳糖苷-β的合成-d-吡喃葡萄糖苷，甲基3- O-（2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基-β-d-吡喃半乳糖苷，甲基3- O-（2-乙酰氨基-2-脱氧-4- O-β -d-吡喃半乳糖基-β-d-吡喃吡喃糖基）-β-d-吡喃半乳糖苷和甲基4-O-[3-O-（2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖基-β- d-吡喃葡萄糖基）-β-d-吡喃半乳糖基]-β-d-吡喃葡糖苷。

  DOI：

  10.1016/0008-6215(85)85219-8

文献信息

• A Novel, Readily Accessible Lactosaminyl Donor:<i>N</i>-Trichloroethoxycarbonyl-hexa-<i>O</i>-benzoyl-<i>β</i>-D-lactosaminyl Fluoride
  作者：Eisuke Kaji、Frieder W. Lichtenthaler、Yumiko Osa、Shonosuke Zen

  DOI：10.1246/bcsj.68.1172

  日期：1995.4

  A simple, preparatively satisfactory 10-step sequence is described for converting lactose into a novel, suitably blocked lactosaminyl donor: N-Trichloroethoxycarbonyl-β-d-lactosaminyl fluoride (5). The key intermediate in this conversion is the particularly well-accessible oxime of lactosulosyl bromide (52% for the 6 steps from lactose), which on α-glycosidation with p-methoxybenzyl alcohol, oxime reduction, N-protection by Troc chloride, and the anomeric fluorination yields 5 (37% for the 4 steps). The utility of 5 as an effective donor was proved by the β-selective glycosylation of the primary 6-OH of 1,2 : 3,4-di-O-isopropylidene-α-d-galactopyranose (14) and the 3-OH of methyl 2,4,6-tri-O-benzyl-β-d-galactopyranoside (16), both affording the respective trisaccharides 15 and 18 in high yields. The latter, when subjected to N-deprotection, N-acetylation, and de-O-acylation gave, in 42% yield based on donor 5, β-d-Gal-(1→4)-β-d-GlcNAc-(1→3)-β-d-Gal-(1→Me, a core trisaccharide unit of immunologically important carbohydrate antigens.

  本文描述了一种简单、制备令人满意的 10 步序列，用于将乳糖转化为一种新型的、适当封端的乳糖胺基供体：N-Trichloroethoxycarbonyl-β-d-lactosaminyl fluoride (5)。这种转化的关键中间体是特别容易获得的溴化乳糖基肟（从乳糖开始的 6 个步骤中占 52%），在与对甲氧基苄醇进行α-糖苷化、肟还原、三氯乙烷的 N 保护和异构体氟化后，可得到 5（4 个步骤中占 37%）。1,2 : 3,4-二-O-异亚丙基-α-d-吡喃半乳糖的初级 6-OH（14）和甲基 2,4,6-三-O-苄基-β-d-吡喃半乳糖苷的 3-OH（16）的β-选择性糖基化证明了 5 是一种有效的供体，两者都能以高产率得到相应的三糖 15 和 18。后者经过 N-脱保护、N-乙酰化和去 O-乙酰化后，以 42% 的产率（基于供体 5）得到了β-d-Gal-(1→4)-β-d-GlcNAc-(1→3)-β-d-Gal-(1→Me)，这是免疫学上重要的碳水化合物抗原的核心三糖单元。
• Synthesis of di-, tri-, and tetra-saccharides corresponding to receptor structures recognised by Streptococcus pneumoniae
  作者：Jan Dahmén、Gösta Gnosspelius、Ann-Charlott Larsson、Thomas Lave、Ghazi Noori、Karin P»lsson、Torbjörn Frejd、Göran Magnusson

  DOI：10.1016/0008-6215(85)85219-8

  日期：1985.4

  Syntheses are described for methyl 2-acetamido-2-deoxy-4- O -β- d -galactopyranosyl-α- d -glucopyranoside, methyl 2-acetamido-2-deoxy-4- O -β- d -galactopyranosyl-β- d -glucopyranoside, methyl 3- O -(2-acetamido-2-deoxy-β- d -glucopyranosyl-β- d -galactopyranoside, methyl 3- O -(2-acetamido-2-deoxy-4- O -β- d -galactopyranosyl-β- d -glucopyranosyl)-β- d -galactopyranoside, and methyl 4- O -[3- O -(2-acetamido-2-deoxy-4-

  摘要描述了甲基2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖苷-α-d-吡喃葡萄糖苷，甲基2-乙酰氨基-2-脱氧-4- O-β-d-吡喃半乳糖苷-β的合成-d-吡喃葡萄糖苷，甲基3- O-（2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基-β-d-吡喃半乳糖苷，甲基3- O-（2-乙酰氨基-2-脱氧-4- O-β -d-吡喃半乳糖基-β-d-吡喃吡喃糖基）-β-d-吡喃半乳糖苷和甲基4-O-[3-O-（2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖基-β- d-吡喃葡萄糖基）-β-d-吡喃半乳糖基]-β-d-吡喃葡糖苷。
• Synthesis of methyl O-(2-O-methyl-β-d-galactopyranosyl)-(1 → 4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)- β-d-galactopyranoside and 4-nitrophenyl O-β-d-galactopyranosyl-(1 → 4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)-β-d-galactopyranoside
  作者：Shaheer H. Khan、Rakesh K. Jain、Khushi L. Matta

  DOI：10.1016/0008-6215(90)80053-6

  日期：1990.8