ethyl 4,6-O-benzylidene-2,3-di-O-para-methoxybenzyl-1-thio-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,6-O-benzylidene-2,3-di-O-para-methoxybenzyl-1-thio-β-D-galactopyranoside
• 英文别名: (4aR,6S,7R,8S,8aS)-6-ethylsulfanyl-7,8-bis[(4-methoxyphenyl)methoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• 化学式: C₃₁H₃₆O₇S
• 分子量: 552.689
• InChiKey: FYUAKXRVVZLZRU-NZJXGLCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-O-benzylidene-2,3-di-O-para-methoxybenzyl-1-thio-β-D-galactopyranoside 在 4 A molecular sieve 、 四丁基溴化铵 、 sodium hydride 、 溶剂黄146 、 copper(ll) bromide 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.0h， 生成 Mob(-2)[Mob(-3)][Bn(-4)][Bn(-6)]Gal(a1-3)[Bn(-2)][Bn(-4)]a-Rha1Me
  参考文献：
  名称：

  Preparation oftransDiequatorial 2,3-Pyruvate Acetals in a Di- and a Trisaccharide Related to the K-Antigen from E. Coli 0101:K103:H⁻

  摘要：

  Using methyl 2,2-bis(ethylthio)propionate as acetalating agent and triflic acid-sulfuryl chloride as catalyst, synthesis of 2,3-trans diequatorial pyruvate ketal was achieved. Starting from D-galactose and L-rhamnose derivatives, methyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1-->4)-6-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene- alpha-D-galactopyranosyl- (1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside and methyl 4,6-di-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene-alpha-D-galactopyranosyl-(1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside were synthesized. Removal of the protecting groups from the former, afforded the trisaccharide repeating unit of the K-antigen from E.coli O101:K103:H- in the form of its methyl glycoside methyl ester.

  DOI：

  10.1080/00397919808006846
• 作为产物：
  描述：

  乙基 4,6-O-亚苄基硫代-beta-D-半乳糖苷 、 4-甲氧基氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以91%的产率得到ethyl 4,6-O-benzylidene-2,3-di-O-para-methoxybenzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation oftransDiequatorial 2,3-Pyruvate Acetals in a Di- and a Trisaccharide Related to the K-Antigen from E. Coli 0101:K103:H⁻

  摘要：

  Using methyl 2,2-bis(ethylthio)propionate as acetalating agent and triflic acid-sulfuryl chloride as catalyst, synthesis of 2,3-trans diequatorial pyruvate ketal was achieved. Starting from D-galactose and L-rhamnose derivatives, methyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1-->4)-6-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene- alpha-D-galactopyranosyl- (1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside and methyl 4,6-di-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene-alpha-D-galactopyranosyl-(1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside were synthesized. Removal of the protecting groups from the former, afforded the trisaccharide repeating unit of the K-antigen from E.coli O101:K103:H- in the form of its methyl glycoside methyl ester.

  DOI：

  10.1080/00397919808006846

文献信息

• Dicarboxymethylated glycolipid derivatives as cell adhesion inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US05686426A1

  公开（公告）日：1997-11-11

  There is provided a novel series of O-carboxymethylated .alpha.- and .beta.-glycolipid compounds of the formula ##STR1## wherein R is an acyl residue of a fatty acid; R.sup.1 is --(CH.dbd.CH).sub.m --(CH.sub.2).sub.n --CH.sub.3 ; R.sup.2, R.sup.3, R.sup.4 R.sup.5 and R.sup.6 each are independently hydrogen, unsubstituted or substituted alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from halogen, C.sub.1-4 alkyl, trifluoromethyl, hydroxy and C.sub.1-4 alkoxy; R.sup.3, R.sup.4 and R.sup.6 each are independently --CH.sub.2 COOR.sup.7, provided at least two of the R.sup.3, R.sup.4 and R.sup.6 substituents are --CH.sub.2 COOR.sub.7 ; m is an integer of 0 or 1; n is an integer of from 5 to 14, inclusive; and R.sup.7 is hydrogen, a hydrolyzable ester group or a cation to form a non-toxic pharmaceutically acceptable salt; or a solvate or hydrate thereof which are inhibitors of selectin-mediated cellular adhesion and are useful in the treatment or prevention of inflammatory diseases and other pathological conditions in mammals.

  提供了一种新颖的一系列O-羧甲基化的α-和β-糖脂化合物，其化学式为##STR1##其中R是脂肪酸的酰基残基；R.sup.1是--(CH.dbd.CH).sub.m--(CH.sub.2).sub.n--CH.sub.3；R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6分别独立地是氢、未取代或取代的烷酰基、芳基烷基或芳基羰基，其中所述取代基选自卤素、C.sub.1-4烷基、三氟甲基、羟基和C.sub.1-4烷氧基；R.sup.3、R.sup.4和R.sup.6分别独立地是--CH.sub.2COOR.sup.7，至少有两个R.sup.3、R.sup.4和R.sup.6取代基是--CH.sub.2COOR.sub.7；m是0或1的整数；n是从5到14的整数，包括在内；R.sup.7是氢、可水解酯基或阳离子，形成非毒性且药学上可接受的盐；或其溶剂合物或水合物，这些化合物是选择素介导的细胞粘附抑制剂，可用于治疗或预防哺乳动物的炎症性疾病和其他病理状况。
• Malonate derivatives of glycolipids as cell adhesion inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US05747463A1

  公开（公告）日：1998-05-05

  There is provided a novel series of malonate derivatives of glycolipid compounds of the formula ##STR1## wherein R is an acyl residue of a fatty acid: R.sup.1 is --(CH.dbd.CH).sub.m --(CH.sub.2).sub.n --CH.sub.3 ; R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 each are independently hydrogen, unsubstituted or substituted (lower)alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from the group consisting of halogen, C.sub.1-4 alkyl, trifluoromethyl, hydroxy and C.sub.1-4 alkoxy provided that one of R.sup.2, R.sup.3, R.sup.4 and R.sup.6 substituents is --(CH.sub.2).sub.p --CH(CO.sub.2 R.sup.7).sub.2 ; m is an integer of 0 or 1; n is an integer of from 5 to 14 inclusive; p is an integer of from 2 to 6 inclusive; and R.sup.7 is hydrogen, a hydrolyzable ester group or a cation to form a non-toxic pharmaceutically acceptable salt; or a solvate or hydrate thereof which are inhibitors of selectin-mediated cellular adhesion and are useful in the treatment or prevention of inflammatory diseases and other pathological conditions in mammals.

  提供了一系列新颖的甘油脂衍生物的马隆酸衍生物，其化学式为##STR1##其中，R是脂肪酸的酰基残基：R.sup.1是--(CH.dbd.CH).sub.m--(CH.sub.2).sub.n--CH.sub.3; R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6各自独立地为氢、未取代或取代的(较低)烷酰基、芳基烷基或芳基羰基，其中所述取代基从卤素、C.sub.1-4烷基、三氟甲基、羟基和C.sub.1-4烷氧基的群中选择，前提是R.sup.2、R.sup.3、R.sup.4和R.sup.6中的一个取代基是--(CH.sub.2).sub.p--CH(CO.sub.2R.sup.7).sub.2; m是0或1的整数；n是从5到14的整数，包括14；p是从2到6的整数，包括6；和R.sup.7是氢、可水解酯基或阳离子，以形成非毒性药学可接受盐；或其溶剂化合物或水合物，这些化合物是选择素介导的细胞黏附抑制剂，并且在哺乳动物的炎症性疾病和其他病理条件的治疗或预防中有用。
• US5686426A
  申请人：——

  公开号：US5686426A

  公开（公告）日：1997-11-11
• US5747463A
  申请人：——

  公开号：US5747463A

  公开（公告）日：1998-05-05
• Preparation of<i>trans</i>Diequatorial 2,3-Pyruvate Acetals in a Di- and a Trisaccharide Related to the K-Antigen from E. Coli 0101:K103:H⁻
  作者：Anup Kumar Misra、Saibal Kumar Das、Nirmolendu Roy

  DOI：10.1080/00397919808006846

  日期：1998.4

  Using methyl 2,2-bis(ethylthio)propionate as acetalating agent and triflic acid-sulfuryl chloride as catalyst, synthesis of 2,3-trans diequatorial pyruvate ketal was achieved. Starting from D-galactose and L-rhamnose derivatives, methyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1-->4)-6-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene- alpha-D-galactopyranosyl- (1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside and methyl 4,6-di-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene-alpha-D-galactopyranosyl-(1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside were synthesized. Removal of the protecting groups from the former, afforded the trisaccharide repeating unit of the K-antigen from E.coli O101:K103:H- in the form of its methyl glycoside methyl ester.