phenyl 1-thio-β-D-gulopyranoside | 1163254-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 1-thio-β-D-gulopyranoside
• 英文别名: Phenyl-1-thio-beta-d-glucopyranoside；(2R,3R,4R,5R,6S)-2-(hydroxymethyl)-6-phenylsulfanyloxane-3,4,5-triol
• CAS: 1163254-75-8
• 化学式: C₁₂H₁₆O₅S
• 分子量: 272.322
• InChiKey: OVLYAISOYPJBLU-ROHXPCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 1-thio-β-D-gulopyranoside 生成 phenyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  FERNANDEZ-MAYORALAS, ALFONSO;MARRA, ALBERTO;TRUMTEL, MICHEL;VEYRIERES, AL+, TETRAHEDRON LETT., 30,(1989) N9, C. 2537-2540

  摘要：

  DOI：

文献信息

• Stereodirecting Effect of the Pyranosyl C-5 Substituent in Glycosylation Reactions
  作者：Jasper Dinkelaar、Ana Rae de Jong、Robert van Meer、Mark Somers、Gerrit Lodder、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo900662v

  日期：2009.7.17

  The stereodirecting effect of the glycosyl C-5 substituent has been investigated in a series of D-pyranosyl thioglycoside donors and related to their preferred positions in the intermediate H-3(4) and H-4(3) half-chair oxacarbenium ions. Computational studies showed that an axially positioned C-5 carboxylate ester can stabilize the (3)H4 half-chair oxacarbenium ion conformer by donating electron densit from its carbonyl function into the electron-poor oxacarbenium ion functionality. A similar stabilization can be achieved by a C-5 benzyloxyrnethyl group, but,the magnitude of this stabilization is significantly smaller than for the C-5 carboxylate ester. As a result, the preference of the C-5 benzyloxymethyl to occupy an axial position in the half-chair oxacarbenium ions is much reduced compared to the C-5 carboxylate ester. To minimize steric interactions, a C-5 methyl group prefers to adopt an equatorial position and therefore favors the H-4(3) half-chair oxacarbenium ion. When all pyranosyl substituents occupy their favored position in one of the two intermediate half-chair oxacarbenium ions, highly stereoselective glycosylations can be achieved as revealed by the excellent beta-selectivity of mannuronate esters and alpha-selectivity of 6-deoxygulosides.
• FERNANDEZ-MAYORALAS, ALFONSO;MARRA, ALBERTO;TRUMTEL, MICHEL;VEYRIERES, AL+, CARBOHYDR. RES., 188,(1989) C. 81-95
  作者：FERNANDEZ-MAYORALAS, ALFONSO、MARRA, ALBERTO、TRUMTEL, MICHEL、VEYRIERES, AL+

  DOI：——

  日期：——
• PEDRETTI, VALERIE;VEYRIERES, ALAIN;SINAY, PIERRE, TETRAHEDRON, 46,(1990) N, C. 77-88
  作者：PEDRETTI, VALERIE、VEYRIERES, ALAIN、SINAY, PIERRE

  DOI：——

  日期：——
• CATELANI, GIORGIO;COLONNA, FABRIZIA;MARRA, ALBERTO, CARBOHYDR. RES., 182,(1988) N 2, C. 297-300
  作者：CATELANI, GIORGIO、COLONNA, FABRIZIA、MARRA, ALBERTO

  DOI：——

  日期：——
• [EN] METHOD FOR THE SYNTHESIS OF SIALYLATED OLIGOSACCHARIDE DONORS<br/>[FR] PROCEDE DE SYNTHESE DE DONNEURS D'OLIGOSACCHARIDE AYANT SUBI UNE SIALYLATION
  申请人：CA NAT RESEARCH COUNCIL

  公开号：WO2001042264A1

  公开（公告）日：2001-06-14

  A method for the synthesis of aryl thioglycosides comprising a sialylated residue of β-D-galactose is disclosed. The method consists of preparing by a chemical synthesis a non-sialylated aryl thioglycoside, and enzymatically sialylating the latter with a sialic acid in the presence of a suitable sialyltransferase. The sialylated aryl thioglycoside is then chemically derivatized by standard procedures, to provide a derivative suitable for use as a donor in chemical syntheses of sialylated oligosaccharides. The derivatized sialylated aryl thioglycosides are prepared in high yields, due to reduced number of chemical and purification steps involved in the process. Derivatized aryl thioglycosides useful as building blocks for the synthesis of biologically active sialylated oligosaccharides are also disclosed.