tert-Butyldimethylsilyl-O-<6-O--β-D-galactopyranosyl>-(1->4)-2-azido-2-desoxy-6-O--β-D-glucopyranosid | 152554-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyldimethylsilyl-O-<6-O--β-D-galactopyranosyl>-(1->4)-2-azido-2-desoxy-6-O--β-D-glucopyranosid
• CAS: 152554-41-1
• 化学式: C₃₄H₇₁N₃O₁₀Si₃
• 分子量: 766.208
• InChiKey: HJOWKIFRVJKKLD-VCVFUBNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  50.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  185.06
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  tert-Butyldimethylsilyl-O-<6-O--β-D-galactopyranosyl>-(1->4)-2-azido-2-desoxy-6-O--β-D-glucopyranosid 在 三氟甲磺酸三甲基硅酯 D(+)-10-樟脑磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 tert-butyldimethylsilyl-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->2)-O-<6-O--3,4-O-isopropyliden-β-D-galactopyranosyl>-(1->4)-2-azido-2-desoxy-6-O--β-D-glucopyranosid
  参考文献：
  名称：

  Kohlenhydrat-Bausteine zum Aufbau Tumor-assoziierter Antigene. Synthese von Lewis Y-Determinanten

  摘要：

  The synthesis of the ethoxycarbonyloctanyl glycoside of the Lewis-Y (Le(y)) tetrasaccharide, a part of complex glycosphingolipids, was based on the trichloroacetimidate method for glycoside synthesis. The regioselective introduction of protective groups and the high yield of epimers of the azidonitration reaction applied to O-(2,3,4-tri-O-acetyl-6-0-[dimethyl-(2,3-dimethyl-2-butyl)silyl]-beta-D-galactopyr-anosyl}-(1 --> 4)-3-0-acetyl-1,5-anhydro-6-0-[dimethyl-(2,3-dimethyl-2-butyl)silyl]-D-arabino-hex-1-enitol led to a lactosamine acceptor molecule. The double specific introduction of an alpha-L-fucosyl group in high yield gave a protected Le(y)-tetrasaccharide. After activation to give the alpha-trichloroacetimidate, specific beta-glycosylation with 8-ethoxycarbonyl octanol under S(N) 2 condition, followed by cleavage of all protective groups led to the tetrasaccharide, alpha-L-Fuc p-(l --> 2)-beta-D-Gal p-(1 --> 4)-[alpha-L-Fuc p-(l --> 3)]-beta-D-Glc pNAcO(CH2)8CO2Et in high yield.

  DOI：

  10.1016/0008-6215(93)80072-m
• 作为产物：
  描述：

  Acetic acid (4R,5S,6R)-3-azido-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-2-nitrooxy-5-{(2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-tetrahydro-pyran-2-yloxy}-tetrahydro-pyran-4-yl ester 在 咪唑 、 sodium methylate 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 tert-Butyldimethylsilyl-O-<6-O--β-D-galactopyranosyl>-(1->4)-2-azido-2-desoxy-6-O--β-D-glucopyranosid
  参考文献：
  名称：

  Kohlenhydrat-Bausteine zum Aufbau Tumor-assoziierter Antigene. Synthese von Lewis Y-Determinanten

  摘要：

  The synthesis of the ethoxycarbonyloctanyl glycoside of the Lewis-Y (Le(y)) tetrasaccharide, a part of complex glycosphingolipids, was based on the trichloroacetimidate method for glycoside synthesis. The regioselective introduction of protective groups and the high yield of epimers of the azidonitration reaction applied to O-(2,3,4-tri-O-acetyl-6-0-[dimethyl-(2,3-dimethyl-2-butyl)silyl]-beta-D-galactopyr-anosyl}-(1 --> 4)-3-0-acetyl-1,5-anhydro-6-0-[dimethyl-(2,3-dimethyl-2-butyl)silyl]-D-arabino-hex-1-enitol led to a lactosamine acceptor molecule. The double specific introduction of an alpha-L-fucosyl group in high yield gave a protected Le(y)-tetrasaccharide. After activation to give the alpha-trichloroacetimidate, specific beta-glycosylation with 8-ethoxycarbonyl octanol under S(N) 2 condition, followed by cleavage of all protective groups led to the tetrasaccharide, alpha-L-Fuc p-(l --> 2)-beta-D-Gal p-(1 --> 4)-[alpha-L-Fuc p-(l --> 3)]-beta-D-Glc pNAcO(CH2)8CO2Et in high yield.

  DOI：

  10.1016/0008-6215(93)80072-m