N-[(2S,3R,4R,5R,6R)-4-[[(3aS,4R,6R,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-[(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-hydroxy-6-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl]benzenesulfonamide | 165816-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5R,6R)-4-[[(3aS,4R,6R,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-[(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-hydroxy-6-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl]benzenesulfonamide
• CAS: 165816-45-5
• 化学式: C₁₃₈H₁₆₉NO₃₀SSi₂
• 分子量: 2410.09
• InChiKey: VZEOJBAZNBYETJ-CHXHAAQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.8
• 重原子数：
  172
• 可旋转键数：
  61
• 环数：
  19.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  332
• 氢给体数：
  2
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5R,6R)-4-[[(3aS,4R,6R,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-[(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-hydroxy-6-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl]benzenesulfonamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到
  参考文献：
  名称：

  Immunization of Mice with a Fully Synthetic Globo H Antigen Results in Antibodies against Human Cancer Cells: A Combined Chemical—Immunological Approach to the Fashioning of an Anticancer Vaccine

  摘要：

  DOI：

  10.1002/anie.199701251
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4-carbonyl-6-O-tri-isopropylsilyl-β-D-galactopyranosyl-(1->3)-6-O-tri-isopropylsilyl-2-deoxy-2-phenylsulfonlyamino-1-thio-β-D-galactopyranoside 、 (2R,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-ol 在 4 A molecular sieve 、 三氟甲烷磺酸甲酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 、 N-[(2S,3R,4R,5R,6R)-4-[[(3aS,4R,6R,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-[(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl]oxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-hydroxy-6-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl]benzenesulfonamide
  参考文献：
  名称：

  人类乳腺肿瘤 (Globo-H) 抗原的全合成和结构证明

  摘要：

  Hakomori MBr1 抗原的全合成，在人类乳腺肿瘤上大量表达，是相关的。该构建涉及四种糖基的组装：（17（两次）、18、20 和 26）和 l-岩藻糖衍生物，34。作为状态函数的末端半乳糖环磺酰氨基半乳糖基化立体化学的敏感性在关键步骤中利用其C4醇的保护状态。（参见化合物 51 的形成。）该合成用于确认 Hakomori 结构的分配，并为免疫偶联铺平了道路。（见化合物 64。）

  DOI：

  10.1021/ja962048b

文献信息

• Total Synthesis and Proof of Structure of a Human Breast Tumor (Globo-H) Antigen
  作者：Tae Kyo Park、In Jong Kim、Shuanghua Hu、Mark T. Bilodeau、John T. Randolph、Ohyun Kwon、Samuel J. Danishefsky

  DOI：10.1021/ja962048b

  日期：1996.1.1

  The total synthesis of the Hakomori MBr1 antigen, heavily expressed on human breast tumors, is related. The construction involved the assembly of four glycals: (17 (twice), 18, 20, and 26) and an l-fucose derivative, 34. The sensitivity of the stereochemistry of sulfonamido galactosylation by a terminal galactose ring as a function of the state of protection status of its C4 alcohol was exploited in

  Hakomori MBr1 抗原的全合成，在人类乳腺肿瘤上大量表达，是相关的。该构建涉及四种糖基的组装：（17（两次）、18、20 和 26）和 l-岩藻糖衍生物，34。作为状态函数的末端半乳糖环磺酰氨基半乳糖基化立体化学的敏感性在关键步骤中利用其C4醇的保护状态。（参见化合物 51 的形成。）该合成用于确认 Hakomori 结构的分配，并为免疫偶联铺平了道路。（见化合物 64。）
• Immunization of Mice with a Fully Synthetic Globo H Antigen Results in Antibodies against Human Cancer Cells: A Combined Chemical—Immunological Approach to the Fashioning of an Anticancer Vaccine
  作者：Govindaswami Ragupathi、Tae Kyo Park、Shengle Zhang、In Jong Kim、Linda Graber、Sucharita Adluri、Kenneth O. Lloyd、Samuel J. Danishefsky、Philip O. Livingston

  DOI：10.1002/anie.199701251

  日期：1997.2.3