1,2-bis(((2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methyl)disulfane | 1269658-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-bis(((2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methyl)disulfane
• 英文别名: bis(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-6,6′-disulfide
• CAS: 1269658-10-7
• 化学式: C₅₆H₆₂O₁₀S₂
• 分子量: 959.234
• InChiKey: DUVSVFMRUZSADZ-AOTKYVILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.62
• 重原子数：
  68.0
• 可旋转键数：
  25.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,2-bis(((2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methyl)disulfane 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 二硫化碳 、 sodiumsulfide nonahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以70%的产率得到(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→6)-(methyl2,3,4-tri-O-benzyl-α-D-glucopyranosid) disulfide
  参考文献：
  名称：

  由糖基溴直接合成不对称糖基二硫化物

  摘要：

  已经开发了一种快速一步反应条件，用于从异头糖基溴化物以优异的收率合成不对称异头糖基二硫化物衍生物。

  DOI：

  10.1002/ejoc.202100606
• 作为产物：
  描述：

  methyl 6-S-acetyl-2,3,4-tri-O-benzyl-6-thio-α-D-glucopyranoside 在 甲醇 、 molybdenum(VI) oxychloride 作用下， 反应 112.0h， 以94%的产率得到1,2-bis(((2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methyl)disulfane
  参考文献：
  名称：

  Chemoselective deacylation of functionalized esters catalyzed by dioxomolybdenum dichloride

  摘要：

  Among five different oxidometallic species and two Lewis acids investigated, MoO(2)Cl(2) shows the best catalytic and chemoselective activity for the deacylation of esters in methanol at ambient or elevated temperature. Both high efficiency and chemoselectivity were achieved for substrates bearing different ether or ester groups. Acylated mono and disaccharides can also be selectively deacetylated in good yields, leading to useful carbohydrate templates for further synthetic manipulations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.024

文献信息

• Preparation of glycosyl disulfides and sulfides via the formation of glycosyl Bunte salts as thiol surrogates
  作者：Monalisa Kundu、Anup Kumar Misra

  DOI：10.1016/j.tet.2021.132242

  日期：2021.5

  odourless reaction condition has been developed for the preparation of symmetrical glycosyl disulfide derivatives and aryl glycosyl disulfide derivatives from corresponding glycosyl iodides via formation of glycosyl Bunte salts as thiol surrogates. The reaction has been further extended towards the preparation of glycosyl sulfides derivatives from corresponding Bunte salt in the presence of sodium sulphide

  开发了一种方便的无味反应条件，用于从相应的糖基碘通过形成糖基邦特盐作为硫醇替代物来制备对称糖基二硫醚衍生物和芳基糖基二硫醚衍生物。该反应已进一步扩展到在硫化钠存在下从相应的邦特盐制备糖基硫醚衍生物。大多数反应产率高，适合放大生产。
• Synthesis of α-2-deoxy-ulosides by Michael addition of hex-1-en-3-ones
  作者：Zi-Ping Lin、Fung Fuh Wong、Yen-Bo Chen、Yu-Cheng Lin、Masayuki Kimura、Kimiyoshi Kaneko、Hiroyuki Takayama、Jin Bin Wu、Chun-Hung Lin、Hui-Chang Lin

  DOI：10.1016/j.tet.2012.12.085

  日期：2013.3

  alpha-2-Deoxyulosides were synthesized in moderate to good yields by Michael addition of various O-nucleophiles to hex-1-en-3-ones in the presence of NaOH. These glycosyl additions were complete in 30 min at room temperature with high alpha-stereoselectivity in 53-92% yield. In addition, high alpha-stereoselectivity was also observed when S-nucleophiles were examined at 0 degrees C for 90 min. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.