methyl 3-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside | 64951-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside
• 英文别名: methyl 3-O-benzyl-2-deoxy-alpha-D-ribo-hexopyranoside；(2R,3S,4S,6S)-2-(hydroxymethyl)-6-methoxy-4-phenylmethoxyoxan-3-ol
• CAS: 64951-98-0
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: SUCQKLFJRXIAOU-CRWXNKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 Methyl 3-O-benzyl-2,6-dideoxy-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Deleterious effect of 7-methyl group on glycosylation of 2-naphthols

  摘要：

  C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (I). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-naphthol (6) embodying the target are ineffective under different Lewis acidic conditions. The inefficiency of the glycosylation of 6 has been attributed to the steric effect exerted by C7 methyl group, which was corroborated by glycosylation studies of different 2-naphthols. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.045
• 作为产物：
  描述：

  methyl 3-O-benzyl-4,6-O-benzylideno-2-deoxy-α-D-ribo-hexoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 methyl 3-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  甲基3-0-苄基-2,4,6-三苯氧基-6-碘-α-d-己吡喃糖苷，用于合成HMG-CoA还原酶抑制剂的手性合成子

  摘要：

  由D-葡萄糖制备甲基3-0-苄基-2,4,6-三苯氧基-6-碘-α-D-己吡喃糖苷，并证明其具有潜在的手性合成子，可用于制备HMG-CoA还原酶抑制剂。

  DOI：

  10.1016/s0040-4039(00)86809-4

文献信息

• Methyl 3-0-benzyl-2,4,6-trideoxy-6-iodo-α-d--hexopyranoside, a chiral synthon for the synthesis of inhibitors of HMG-CoA reductase
  作者：John D. Prugh、Albert A. Deana

  DOI：10.1016/s0040-4039(00)86809-4

  日期：1982.1

  Methyl 3-0-benzyl-2,4,6-trideoxy-6-iodo-α-D--hexopyranoside was prepared from D-glucose and demonstrated to have potential utility as a chiral synthon for the elaboration of HMG-CoA reductase inhibitors.

  由D-葡萄糖制备甲基3-0-苄基-2,4,6-三苯氧基-6-碘-α-D-己吡喃糖苷，并证明其具有潜在的手性合成子，可用于制备HMG-CoA还原酶抑制剂。
• Process for preparing inhibitors of 3-hydroxy-3-methylglutaryl coenzyme
  申请人：Merck & Co., Inc.

  公开号：US04440927A1

  公开（公告）日：1984-04-03

  Totally synthetic analogs of the known inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase, compactin and mevinolin, are prepared from a chiral synthon derived from D-glucose which has the same chirality as the natural products.

  完全合成的3-羟基-3-甲基戊二酰辅酶A还原酶抑制剂compactin和mevinolin的类似物，是由从D-葡萄糖衍生的手性合成物制备而成，其手性与天然产物相同。
• Ferro, Vito; Skelton, Brian W.; Stick, Robert V., Australian Journal of Chemistry, 1993, vol. 46, # 6, p. 787 - 803
  作者：Ferro, Vito、Skelton, Brian W.、Stick, Robert V.、White, Allan H.

  DOI：——

  日期：——
• Synthesis and utilization of the chiral synthon methyl 3-O-benzyl-2,4,6-trideoxy-6-iodo-.alpha.-D-erythro-hexopyranoside in the synthesis of a potent HMG-CoA reductase inhibitor
  作者：John D. Prugh、C. Stanley Rooney、Albert A. Deana、Harri G. Ramjit

  DOI：10.1021/jo00355a014

  日期：1986.3
• BERGMANN, ANDREAS;BARTMANN, WILHELM;BECK, GERHARD;LAU, HANS-GERMANN
  作者：BERGMANN, ANDREAS、BARTMANN, WILHELM、BECK, GERHARD、LAU, HANS-GERMANN

  DOI：——

  日期：——