phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside | 89387-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 89387-42-8
• 化学式: C₃₅H₃₆O₆S
• 分子量: 584.733
• InChiKey: LAWHWGUHXVVWIF-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 丙酮 为溶剂， 反应 0.06h， 以91%的产率得到4-O-acetyl-2,3,6-tri-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  6‴-α-麦芽三糖基-麦芽六糖的化学合成作为淀粉生物合成和降解中酶的底物

  摘要：

  6-三-O-苄基-1-硫代-β-D-吡喃葡萄糖苷，得到过-O-苄基化的支链九糖苯基硫代糖苷。用游离的OH-基取代苯硫基，然后进行氢解，得到所需的产物。报告用于该合成的合成子构成用于其他复杂碳水化合物的化学合成的通用工具。

  DOI：

  10.1016/s0008-6215(99)00131-7
• 作为产物：
  描述：

  2,3-双-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代-B-D-吡喃葡萄糖苷苯酯 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

  摘要：

  Glucosylations and galactosylations of various acceptors with donors possessing an electronwithdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A beta-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an alpha-directing effect. The alpha-directing effect is partly considered to remote participation of the acyl groups, whereas the beta-directing effect is somewhat attributed to the S(N)2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the alpha-glycosyl triflates was determined by a low-temperature NMR study. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.014

文献信息

• Stereospecific synthesis of rhynchosporosides, a family of fungal metabolites causing scald disease in barley and other grasses
  作者：K. C. Nicolaou、J. L. Randall、G. T. Furst

  DOI：10.1021/ja00305a056

  日期：1985.9
• Synthetic studies on rhynchosporoside: Stereoselective synthesis of 1-O- and 2-O-α-cellotriosyl-3-deoxy-2(R)- and -2(S)-glycerol
  作者：Fumio Sugawara、Haruhiko Nakayama、Tomoya Ogawa

  DOI：10.1016/0008-6215(83)88494-8

  日期：1983.11