Benzyl 5-Acetamido-4,7,8,9-tetra-O-benzyl-7-hydroxy-3,5-dideoxy-D-glycero-D-galacto-2-non-enoate | 130841-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 5-Acetamido-4,7,8,9-tetra-O-benzyl-7-hydroxy-3,5-dideoxy-D-glycero-D-galacto-2-non-enoate
• 英文别名: benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate；benzyl (2R,3R,4S)-3-acetamido-4-phenylmethoxy-2-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 130841-39-3
• 化学式: C₄₆H₄₇NO₈
• 分子量: 741.881
• InChiKey: DATOSLSJLPFTJX-ZHMYNSSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Benzyl 5-Acetamido-4,7,8,9-tetra-O-benzyl-7-hydroxy-3,5-dideoxy-D-glycero-D-galacto-2-non-enoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 1.5h， 生成 (2R,3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-hydroxy-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment

  摘要：

  Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide la. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00172-1
• 作为产物：
  描述：

  (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-(toluene-4-sulfinyl)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester 以 甲苯 为溶剂， 以64%的产率得到Benzyl 5-Acetamido-4,7,8,9-tetra-O-benzyl-7-hydroxy-3,5-dideoxy-D-glycero-D-galacto-2-non-enoate
  参考文献：
  名称：

  An efficient method for the preparation of 2-hydroxy- and 2-aminoglycals from glycosyl sulfoxides

  摘要：

  A new and efficient route to 2-hydroxy- and 2-aminoglycals from glycosyl sulfoxides has been developed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00555-5

文献信息

• Synthesis of Pyrrolidine Analogues ofN-Acetylneuraminic Acid as Potential Sialidase Inhibitors
  作者：L�szl� Czollner、J�nos Kuszmann、Andrea Vasella

  DOI：10.1002/hlca.19900730522

  日期：1990.8.8

  The pyrrolidine derivatives 3, 4, and 5 were prepared from the methyl ester 7 of Neu2en5Ac via lie pyrrolidine-borane adduct 33. They inhibit Vibrio cholerae sialidase competitively with Ki = 4. 4 10−3 M, 5. 3 10−3 M, and 4. 0 10−2 M, respectively. Benzylation of 7 gave the fully O-benzylated 8 besides 9, 10, and 11. Ozonolysis and reduction with NaBH4 of 8 and 9 gave the 1, 4-diols 12 and 15, the

  的吡咯烷衍生物3，4和5是从甲基酯制备7 Neu2en5Ac的经由谎言吡咯烷甲硼烷加成物33。它们分别以K i分别为4. 4 10 -3 M，5。3 10 -3 M和4. 0 10 -2 M抑制霍乱弧菌唾液酸酶。的苄基化7得到充分ø -benzylated 8除了9,10，和11臭氧分解和还原用NaBH 4的8和9分别得到1，4-二醇12和15，乙酸羟基酯13和16以及呋喃糖酶14和17（方案1）。二醇12被选择性保护（19 20 23），并通过Mitsunobu反应转化为叠氮化物27。容易的乙酰基迁移阻碍了由12获得的双乙酸酯22的选择性碱催化的脱保护。甲磺酸盐28被证明是不稳定的。叠氮化物27转化通过将29引入酮30中（方案2）。氢化30得到二氢吡咯31，因此得到吡咯32。加合物33通过施陶丁格反应（31）并用LiBH 4 / HBF 4还原而从30获得。它被转化为吡咯烷34。通过X射
• CZOLLNER, LASZLO;KUSZYMANN, JANOS;VASELLA, ANDREA, HELV. CHIM. ACTA, 73,(1990) N, C. 1338-1358
  作者：CZOLLNER, LASZLO、KUSZYMANN, JANOS、VASELLA, ANDREA

  DOI：——

  日期：——