ethyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside | 454664-77-8

• 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-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
• CAS: 454664-77-8
• 化学式: C₂₃H₂₈O₆S
• 分子量: 432.538
• InChiKey: UMULJXSSKJYXCM-YPEXMJEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 作用下， 反应 69.67h， 生成 ethyl 4-O-benzyl-2-O-(2,5-difluorobenzoyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Chemical Synthesis of Highly Congested gp120 V1V2 N-Glycopeptide Antigens for Potential HIV-1-Directed Vaccines

  摘要：

  Critical to the search for an effective HIV-1 vaccine is the development of immunogens capable of inducing broadly neutralizing antibodies (BnAbs). A key first step in this process is to design immunogens that can be recognized by known BnAbs. The monoclonal antibody PG9 is a BnAb that neutralizes diverse strains of HIV-1 by targeting a conserved carbohydrate protein epitope in the variable 1 and 2 (V1V2) region of the viral envelope. Important for recognition are two closely spaced N-glycans at Asn(160) and Asn(156). Glycopeptides containing this synthetically challenging bis-N-glycosylated motif were prepared by convergent assembly, and were shown to be antigenic for PG9. Synthetic glycopeptides such as these may be useful for the development of HIV-1 vaccines based on the envelope V1V2 BnAb epitope.

  DOI：

  10.1021/ja405990z
• 作为产物：
  描述：

  4-甲氧基氯苄 、 ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 二正丁基氧化锡 、 四丁基溴化铵 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 ethyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Efficient Installation of β-Mannosides Using a Dehydrative Coupling Strategy

  摘要：

  A new coupling procedure for the construction of the challenging beta-mannosidic bond is described. Dehydrative mannosylation using 4,6-O-benzylidene mannopyranoses allows for the formation of beta-mannosides in excellent yield. The stereoselectivity is generally good but influenced by the exact nature of the glycosylating agent and the nucleophile.

  DOI：

  10.1021/ol051038p

文献信息

• SYNTHESIS OF THE TETRASACCHARIDE Glc α (1→3) Man α (1→2) Man α (1→2) Man α (OMe) AS INHIBITOR OF CALNEXIN BINDING TO GlcMan ₉GlcNAc ₂ ^a
  作者：Slim Cherif、Jean-Marc Clavel、Claude Monneret

  DOI：10.1081/car-120003743

  日期：2002.5.31

  Tetrasaccharide GlcMan(3) is an inhibitor of GlcMan(9)GlcNAc(2) binding to calnexin, a chaperone protein involved in CFTR-DeltaF 508 retention. A convergent route to its methyl glycoside, the title tetrasaccharide, was developed. The key building block Glc alpha (1-->3) Man 6 was stereoselectively obtained by condensation of a trichloroacetimidate glucosyl donor with an ethyl thiomannopyranoside acceptor. Di-mannose moiety 10 and final compound 12 resulted from thioglycoside activations.