2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-galactopyranoside | 191924-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)-6-(2-trimethylsilylethoxy)oxan-3-ol
• CAS: 191924-41-1
• 化学式: C₂₅H₃₆O₆Si
• 分子量: 460.643
• InChiKey: BUXNTEWTBVXRIB-ZLOLNMDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 氢气 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 238.0h， 生成 4-amino-4,6-dideoxy-α-D-glucopyranosyl phosphate
  参考文献：
  名称：

  α-葡萄糖苷酶抑制剂阿卡波糖的生物合成研究：dTDP-4-氨基-4,6-二脱氧-α-D-葡萄糖的化学合成。

  摘要：

  为了研究假四糖阿卡波糖的生物合成，由半乳糖分16步制备了dTDP-4-氨基-4,6-二脱氧-α-D-葡萄糖（3）。在最初的保护基操纵之后，通过甲苯磺酸酯的氢化物置换使半乳糖的6-位脱氧。类似地，在与叠氮化钠反应时，在4-位的甲苯磺酰基被置换。通过使糖基三氯乙酰亚胺酸酯与磷酸二苄基酯反应，将所得的糖苷转化为糖基磷酸酯。随后除去苄基保护基并通过氢化和与活化的核苷磷酸偶合来还原叠氮化物，得​​到dTDP-4-氨基-4,6-二脱氧-α-D-葡萄糖。

  DOI：

  10.1016/s0008-6215(01)00323-8
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-galactopyranoside 在 水 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.25h， 生成 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  α-葡萄糖苷酶抑制剂阿卡波糖的生物合成研究：dTDP-4-氨基-4,6-二脱氧-α-D-葡萄糖的化学合成。

  摘要：

  为了研究假四糖阿卡波糖的生物合成，由半乳糖分16步制备了dTDP-4-氨基-4,6-二脱氧-α-D-葡萄糖（3）。在最初的保护基操纵之后，通过甲苯磺酸酯的氢化物置换使半乳糖的6-位脱氧。类似地，在与叠氮化钠反应时，在4-位的甲苯磺酰基被置换。通过使糖基三氯乙酰亚胺酸酯与磷酸二苄基酯反应，将所得的糖苷转化为糖基磷酸酯。随后除去苄基保护基并通过氢化和与活化的核苷磷酸偶合来还原叠氮化物，得​​到dTDP-4-氨基-4,6-二脱氧-α-D-葡萄糖。

  DOI：

  10.1016/s0008-6215(01)00323-8

文献信息

• A Solution to Chemical Pseudaminylation via a Bimodal Glycosyl Donor for Highly Stereocontrolled α- and β-Glycosylation
  作者：Ruohan Wei、Han Liu、Arthur H. Tang、Richard J. Payne、Xuechen Li

  DOI：10.1021/acs.orglett.9b00990

  日期：2019.5.17

  A robust methodology for the stereocontrolled chemical glycosylation of pseudaminic acid has been developed to afford both α- (axial) and β- (equatorial) glycosides reliably with complete stereoselectivity, using a common glycosyl donor (7N-Cbz/5N-azido Pse thioglycoside) simply by changing the reaction conditions. In the CH2Cl2/MeCN cosolvent, highly β-selective pseudaminylation was observed, while

  已开发出一种可靠的方法对伪氨基酸进行立体控制的化学糖基化反应，可使用常见的糖基供体（7 N -Cbz / 5 N-叠氮基Pse ）可靠地提供α-（轴向）和β-（赤道）糖苷，且具有完全的立体选择性。硫糖苷），只需更改反应条件即可。在CH 2 Cl 2 / MeCN助溶剂中，观察到了高度β-选择性的伪氨基化，而在CH 2 Cl 2中加入5.0当量的DMF则得到了α-伪氨基糖苷。
• A synthetic approach to the c-series gangliosides containing sialyl-α(2 → 8) sialyl-α(2 → 8)sialic acid: Synthesis of ganglioside GT4, α(2 → 6)GT4 and GT3
  作者：Hiromune Ando、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/s0008-6215(97)00051-7

  日期：1997.5

  reducting end, O-acetylation and conversion of the anomeric acetoxy group into a phenylthio group. Iodonium-promoted glycosylation of 3 with 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-beta-D-galactopyranoside (5), 2-(trimethylsilyl)ethyl 3-O-benzyl-beta-D-galactopyranoside (6), 2-(trimethylsilyl)ethyl 2-O-benzoyl-3-O-benzyl-beta-D-galactopyranoside (9), and 2-(trimethylsilyl)ethyl 2, 3-di-O-benzyl-beta-D-galactopyranoside

  三聚唾液酸[Neu5Acα（2-> 8）Neu5Acα（2-> 8）Neu5Ac，1]含残基的神经节苷脂，GT4，α（2-> 6）GT4和GT3已合成用于第一次。甲基[苯基] 5-乙酰氨基-8-O- [5-乙酰氨基-8-O-（5-乙酰氨基-4、7、8、9-四-O-乙酰基-3、5-二脱氧-D-甘油alpha-D-galacto-2-nonulopyranosylono-1“，9'-lactone）-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylono-1通过内酯化由1制备1，9-内酯] -4，7-二-O-乙酰基-3,5-二脱氧-2-硫代-D-甘油-D-半乳糖-2-壬基吡喃糖苷（3）。 ，在还原端羧基的甲基酯化，O-乙酰化和异头乙酰氧基转化为苯硫基。碘鎓促进3与2-（三甲基甲硅烷基）乙基2,6-二-
• Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapGJ96 from Escherichia coli
  作者：Henrik C. Hansen、Göran Magnusson

  DOI：10.1016/s0008-6215(98)00020-2

  日期：1998.2

  The 2'-amino-2'-deoxy, 6-amino-6-deoxy, and 6-carboxy analogs of the reference inhibitor 2-(trimethylsilyl)ethyl (alpha-D-galactopyranosyl)-(1-->4)-beta-D-galactopyranoside were synthesized and evaluated as inhibitors of the binding of the Escherichia coli-derived pilus protein PapG(J96), using an ELISA assay. The inhibitory efficiencies (K-rel; relative to the reference inhibitor) were: 157, 13, and < 8, respectively. The results support the previously proposed combining site model, where the protein carries a negatively charged amino acid residue near HO-2' and HO-6 of the galabioside. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of selected aminodeoxy analogues of galabiose and globotriose
  作者：Henrik C. Hansen、Göran Magnusson

  DOI：10.1016/s0008-6215(99)00229-3

  日期：1999.12

  Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents
  作者：Mohamed R.E. Aly、Pascal Rochaix、Mohamed Amessou、Ludger Johannes、Jean-Claude Florent

  DOI：10.1016/j.carres.2006.03.044

  日期：2006.9

  The galactosyl donor, 4,6-di-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyl trichloroacetimidate, was efficiently coupled with regioselectively benzylated lactoside acceptors under standard conditions to stereoselectively afford the corresponding globotrioside and isoglobotrioside derivatives in very good yields. These glycosides were smoothly functionalized with a 6-(p-cinnamoylplienoxy)-hexyl tether tag as novel electrophilic thiol-specific carbohydrate reagents. Immobilization of the globotrioside conjugate to Thiopropyl Sepharose 6B for purification of B-subunit of Shiga toxin (StxB) and coupling of a model cysteine-containing protein (StxB-Z(n)-Cys) to the isoglobotrioside conjugate were both performed with high efficiency. (c) 2006 Elsevier Ltd. All rights reserved.