Benzoic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-methoxy-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester | 191485-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-methoxy-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester
• CAS: 191485-92-4
• 化学式: C₂₉H₂₉F₃O₉S
• 分子量: 610.605
• InChiKey: XTNOZIAJLRMMQD-BZTMQRDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-methoxy-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester 在 lithium aluminium tetrahydride 、 正丁基锂 、 四丁基溴化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 40.0h， 生成 methyl 2,3-di-O-benzyl-4-S-[(E)-2-(phenylsulfonyl)-vinyl]-4-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Vinyl bis-sulfone methodology in thiosugars: selective access to chiral thiovinyl sulfones and PSE oxathianes

  摘要：

  Based on the vinyl biS-sulfone methodology previously developed to synthesize PSE acetals, an original approach to homochiral carbohydrate-derived PSE 1,3-oxathianes is described. The ready formation of intermediate phenylsul fonyl vinyl sulfides, which have a synthetic potential of their own, emphasizes the versatility of the method. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.023
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-β-D-galactopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 Benzoic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-methoxy-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Vinyl bis-sulfone methodology in thiosugars: selective access to chiral thiovinyl sulfones and PSE oxathianes

  摘要：

  Based on the vinyl biS-sulfone methodology previously developed to synthesize PSE acetals, an original approach to homochiral carbohydrate-derived PSE 1,3-oxathianes is described. The ready formation of intermediate phenylsul fonyl vinyl sulfides, which have a synthetic potential of their own, emphasizes the versatility of the method. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.023

文献信息

• Synthesis of methyl 4-thio-β-cellobioside. A reinvestigation
  作者：Vincent Moreau、Jens Chr. Norrild、Hugues Driguez

  DOI：10.1016/s0008-6215(97)00046-3

  日期：1997.5

  Abstract The best yield for the synthesis of the title compound was obtained by nucleophilic displacement of the 4- O -triflyl group in methyl tri -O- benzyl -4-O- triflyl -β- d - galactopyranoside by 2,3,4,6- tetra -O- acetyl -1-S- acetyl-1-thio -β- d - glucopyranose in HMPA in the presence of diethylamine. Under these conditions, the formation of unsaturated side products was decreased.

  摘要通过亲核置换甲基三-O-苄基-4-O-三flyl-β-d-半乳糖吡喃糖苷中的4-O-三氟甲苯基，可得到2,3,4的最佳收率。在二乙胺存在下，HMPA中的6-四-O-乙酰基-1-S-乙酰基-1-硫代-β-d-吡喃葡萄糖。在这些条件下，减少了不饱和副产物的形成。