benzyl 6-O-β-D-galactopyranosyl-β-D-galactopyranoside | 120094-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-O-β-D-galactopyranosyl-β-D-galactopyranoside
• 英文别名: Gal(b1-6)Gal(b)-O-Bn；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-phenylmethoxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 120094-98-6
• 化学式: C₁₉H₂₈O₁₁
• 分子量: 432.425
• InChiKey: LLEMMFPELBNINR-XHXKXHHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.17
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  178.53
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  benzyl 6-O-β-D-galactopyranosyl-β-D-galactopyranoside 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以15.9 mg的产率得到6-O-β-D-galactopyranosyl-D-galactose
  参考文献：
  名称：

  Synthesis of Model Compounds Related to Linear β-D-(1→6)-Galactosyl Side-Chains of Polysaccharides from Astragalus mongholicus Bunge

  摘要：

  Stereocontrolled efficient syntheses of beta-(1 -> 6)-linked di-, tetra- and octa-galactans as model compounds of arabino-3,6-galactans isolated from Astragalus mongholicus are described. The syntheses consisted of simple glycosylation cycles: an acceptor and a donor prepared from a common compound were coupled, and the glycosylation product was converted to the acceptor and donor of the next glycosylation.

  DOI：

  10.3987/com-14-s(k)61
• 作为产物：
  描述：

  benzyl 2,3,4-tri-O-benzoyl-6-O-levulinoyl-β-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 benzyl 6-O-β-D-galactopyranosyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Model Compounds Related to Linear β-D-(1→6)-Galactosyl Side-Chains of Polysaccharides from Astragalus mongholicus Bunge

  摘要：

  Stereocontrolled efficient syntheses of beta-(1 -> 6)-linked di-, tetra- and octa-galactans as model compounds of arabino-3,6-galactans isolated from Astragalus mongholicus are described. The syntheses consisted of simple glycosylation cycles: an acceptor and a donor prepared from a common compound were coupled, and the glycosylation product was converted to the acceptor and donor of the next glycosylation.

  DOI：

  10.3987/com-14-s(k)61

文献信息

• A simple strategy for changing the regioselectivity of glycosidase-catalysed formation of disaccharides: Part II, enzymic synthesis in situ of various acceptor glycosides
  作者：Kurt G.I. Nilsson

  DOI：10.1016/0008-6215(88)80063-6

  日期：1988.9

  trimethylsilylethanol, respectively. Similarly, α- d -galactosidase catalysed the formation of allyl α- d -galactopyranoside from raffinose and allyl alcohol. The galactosides were used as acceptors for the preparation of the following disaccharide glycosides: β- d -Gal-(1→3)-β- d -Gal-OCH2CHCH2, β- d -Gal-(1→6)-β- d -Gal-OCH2CHCH2, β- d -Gal-(1→3)-β- d -Gal-OBn, β- d -Gal-(1→6)-β- d -Gal-OBn, β- d -Gal-(1→3)-β-

  摘要β-d-半乳糖苷酶分别诱导了乳糖和烯丙醇，苄醇和三甲基甲硅烷基乙醇中1-20g的烯丙基，苄基和三甲基甲硅烷基乙基β-吡喃半乳糖苷的形成。类似地，α-d-半乳糖苷酶催化从棉子糖和烯丙醇形成烯丙基α-d-半乳糖吡喃糖苷。半乳糖苷被用作受体，用于制备以下二糖苷：β-d -Gal-（1→3）-β-d-Gal-O CH = CH2，β-d -Gal-（1→6）-β -d -Gal-O CH = ，β-d -Gal-（1→3）-β-d -Gal-OBn，β-d -Gal-（1→6）-β-d -Gal-OBn，β -d -Gal-（1→3）-β-d-Gal-OCH 2 CH 2 SiMe 3和α-d-Gal-（1→3）-α-d-Gal-OCH 2 CH 3 CH 2。β-d-半乳糖苷酶催化的反应足够有效，可以从乳糖和醇一锅制备各种β-连接的单-和半-半乳糖苷。