Acetic acid (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-(3-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester | 213192-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-(3-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS: 213192-04-2
• 化学式: C₅₆H₆₆N₄O₁₄
• 分子量: 1019.16
• InChiKey: YKEWUZWEULOQPY-NVOPCUPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  74.0
• 可旋转键数：
  29.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  205.69
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-(3-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.33h， 以42%的产率得到Acetic acid (2S,3R,4S,5S,6R)-2-{(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of Le^X and Le^Y Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups

  摘要：

  5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc and the tetrasaccharide alpha-L-Fuc-alpha-(1-->2)-beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc that represent the epitopes defining the human blood groups Le(x) and Le(y). The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.

  DOI：

  10.1080/07328309808007459
• 作为产物：
  描述：

  N-{(4aR,6R,7R,8R,8aS)-6-[2-(2-Azido-ethoxy)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide 在 barium dihydroxide 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 barium(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 Acetic acid (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-(3-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of Le^X and Le^Y Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups

  摘要：

  5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc and the tetrasaccharide alpha-L-Fuc-alpha-(1-->2)-beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc that represent the epitopes defining the human blood groups Le(x) and Le(y). The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.

  DOI：

  10.1080/07328309808007459