p-methoxyphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 409060-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-Ph(4-OMe)；(2S,3R,4S,5R,6R)-2-(4-methoxyphenoxy)-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane
• CAS: 409060-31-7
• 化学式: C₆₈H₇₀O₁₂
• 分子量: 1079.3
• InChiKey: SSNGRUUFJYCHHX-VUURLJBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  80
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranose 、 2,3,6-tri-O-benzyl-4-O-(2′,3′,4′,6′-tetra-O-benzyl-β-D-galactopyranosyl)-D-glucopyranose
  参考文献：
  名称：

  Synthesis of α-lactosyl-(1→3)-l-glycero-α-d-manno-heptopyranoside, a partial oligosaccharide structure expressed within the lipooligosaccharide produced by Neisseria gonorrhoeae strain 15253

  摘要：

  The glycosyl donor, hepta-O-benzyl-beta-lactosyl trichloroacetimidate (4) was prepared by treating hepta-O-benzyl-lactose with trichloroacetonitrile in the presence of potassium carbonate. The acceptor, methyl 2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-alpha-D-manno-oct-7-enopyranoside (8) was synthesized by hydrolysis of a 3,4-butane diacetal of methyl L-glycero-alpha-D-manno-oct-enopyranoside and subsequent benzylidenation, Glycosidation of the donor 4 with the acceptor 8 in 1,4-dioxane using Me3SiOTf as a promoter for I h at room temperature gave methyl (2,3,4,6-tetra-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)-(1-->3)-2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-alpha-D-manno-oct-7-enopyranoside (9) as a major product (59%). The oct-enopyranoside moiety of the trisaccharide 9 was converted to a heptopyranoside (80%) by oxidative cleavage with OsO4-NaIO4 and subsequent reduction. Hydrogenolysis of the resulting trisaccharide and subsequent acetylation gave the peracetate of alpha-lactosyl-(1-->3)-Hep. Deacetylation of the peracetate afforded the title trisaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00282-8
• 作为产物：
  描述：

  溴甲苯 、 4-甲氧苯基-4-O-(β-D-吡喃半乳糖酰基)-β-D-吡喃葡萄糖苷 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到p-methoxyphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of α-lactosyl-(1→3)-l-glycero-α-d-manno-heptopyranoside, a partial oligosaccharide structure expressed within the lipooligosaccharide produced by Neisseria gonorrhoeae strain 15253

  摘要：

  The glycosyl donor, hepta-O-benzyl-beta-lactosyl trichloroacetimidate (4) was prepared by treating hepta-O-benzyl-lactose with trichloroacetonitrile in the presence of potassium carbonate. The acceptor, methyl 2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-alpha-D-manno-oct-7-enopyranoside (8) was synthesized by hydrolysis of a 3,4-butane diacetal of methyl L-glycero-alpha-D-manno-oct-enopyranoside and subsequent benzylidenation, Glycosidation of the donor 4 with the acceptor 8 in 1,4-dioxane using Me3SiOTf as a promoter for I h at room temperature gave methyl (2,3,4,6-tetra-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)-(1-->3)-2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-alpha-D-manno-oct-7-enopyranoside (9) as a major product (59%). The oct-enopyranoside moiety of the trisaccharide 9 was converted to a heptopyranoside (80%) by oxidative cleavage with OsO4-NaIO4 and subsequent reduction. Hydrogenolysis of the resulting trisaccharide and subsequent acetylation gave the peracetate of alpha-lactosyl-(1-->3)-Hep. Deacetylation of the peracetate afforded the title trisaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00282-8

文献信息

• Zinc triflate–benzoyl bromide: a versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides
  作者：Tülay Polat、Robert J. Linhardt

  DOI：10.1016/s0008-6215(02)00481-0

  日期：2003.2

  A simple and efficient method is developed for the chemoselective one-pot conversion of ethers (benzyl, TBDMS and acetal) to the corresponding benzoates by zinc triflate-catalyzed deprotection and benzoylation by benzoyl bromide. In the same reaction, methyl or p-methoxyphenyl glycosides are converted into glycosyl bromides that are useful in glycosylation reactions.

  通过三氟甲磺酸锌催化的脱保护和苯甲酰溴的苯甲酰化，开发了一种简单有效的方法，将醚（苄基，TBDMS和乙缩醛）化学选择性地一锅转化为相应的苯甲酸酯。在同一反应中，甲基或对甲氧基苯基糖苷被转化为可用于糖基化反应的糖基溴化物。
• Synthesis of α-lactosyl-(1→3)-l-glycero-α-d-manno-heptopyranoside, a partial oligosaccharide structure expressed within the lipooligosaccharide produced by Neisseria gonorrhoeae strain 15253
  作者：Kazuyuku Ishii、Hiroyuki Kubo、Ryohei Yamasaki

  DOI：10.1016/s0008-6215(01)00282-8

  日期：2002.1

  The glycosyl donor, hepta-O-benzyl-beta-lactosyl trichloroacetimidate (4) was prepared by treating hepta-O-benzyl-lactose with trichloroacetonitrile in the presence of potassium carbonate. The acceptor, methyl 2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-alpha-D-manno-oct-7-enopyranoside (8) was synthesized by hydrolysis of a 3,4-butane diacetal of methyl L-glycero-alpha-D-manno-oct-enopyranoside and subsequent benzylidenation, Glycosidation of the donor 4 with the acceptor 8 in 1,4-dioxane using Me3SiOTf as a promoter for I h at room temperature gave methyl (2,3,4,6-tetra-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)-(1-->3)-2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-alpha-D-manno-oct-7-enopyranoside (9) as a major product (59%). The oct-enopyranoside moiety of the trisaccharide 9 was converted to a heptopyranoside (80%) by oxidative cleavage with OsO4-NaIO4 and subsequent reduction. Hydrogenolysis of the resulting trisaccharide and subsequent acetylation gave the peracetate of alpha-lactosyl-(1-->3)-Hep. Deacetylation of the peracetate afforded the title trisaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.