(2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate | 121237-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate
• 英文别名: benzyl (4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside；(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,2,3,6-tetra-O-benzyl-β-D-glucopyranose；Bn(-2)[Bn(-6)]Gal4Ac(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-Bn；[(2R,3R,4S,5R,6S)-4-hydroxy-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-[(2R,3R,4S,5R,6R)-4,5,6-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-3-yl] acetate
• CAS: 121237-39-6
• 化学式: C₅₆H₆₀O₁₂
• 分子量: 925.085
• InChiKey: NHIHODJEBQMSMF-ULOPEHTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  68
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate 在 吡啶 、 甲磺酰溴 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 9.0h， 生成 Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid
  参考文献：
  名称：

  Lactotriaose-containing carbosilane dendrimers: Syntheses and lectin-binding activities

  摘要：

  Carbosilane dendrimers periphery-functionalized with lactotriaose (GlcNAc beta 1-3Gal beta l-4Glc) with valencies of three, four, six, and twelve were prepared for use in a lectin-binding assay. A lactotriaose derivative was prepared from D-glucosamine and D-lactose derivatives. The N-Troc-protected glucosamine glycosyl donor and 3'-O-unprotected lactose glycosyl acceptor were condensed in the presence of silver trifluoromethanesulfonate and methylsulfenyl bromide to provide corresponding trisaccharide with new beta-1-3 linkages in 92% yield. The protection group of the trisaccharide was transformed into an acetyl group. The 4-pentenyl glycoside was prepared from the acetate via glycosyl bromide. The alkene was converted into acetyl sulfide by addition of thioacetic acid under radical conditions. The lactotriaose unit was linked with carbosilane dendrimers to afford acelyl-protected glycodendrimers. De-O-acetylation of the dendrimers was carried out in the presence of sodium methoxide and then aq NaOH to give the desired lactotriaose clusters using a carbosilane dendrimer backbone. Their biological activities toward WGA were evaluated by fluorescence methods. The binding constants of free lactotriaose and trivalent, tetravalent, hexavalent, and dodecavalent glycodendrimers to WGA were determined to be 1.1 x 10(3), 4.4 x 10(4), 5.1 x 10(4), 2.8 x 10(6), and 1.3 x 10(6) M-1, respectively. The hexavalent glycodendrimer showed a 2500-fold larger binding effect than that of free lactotriaose. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.030
• 作为产物：
  描述：

  benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 4.42h， 生成 (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  Synthesis of lacto- N -tetraose

  摘要：

  Human milk oligosaccharides (HMOs) are the third largest macromolecular component of breast milk and offer infants numerous health benefits, most of which stem from the development of a healthy microbiome. Characterization, quantification, and chemical derivatization of HMOs remains a frontier issue in glycobiology due to the challenge of isolating appreciable quantities of homogenous HMOs from breast milk. Herein, we report the synthesis of the human milk tetrasaccharide lacto-N-tetraose (LNT). LNT is ubiquitous in human breast milk as it is a core structure common to longer-chain HMOs and many glycolipids. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.02.001

文献信息

• A Convenient Synthesis of Partially Benzylated Derivative of β-DGlcpNAc-( 1→3)-β-D-Galp-(1→4)-β-D-Glcp-1-OBn as a Versatile Building Block for Sialyl Lewis X Antigens
  作者：Sameh Soliman、Rafik Bassily、Ramadan El-Sokkary、Mina Nashed

  DOI：10.2174/1570178612666150415235934

  日期：2015.6.4

  Synthesis of the trisaccharide, benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-Dglucopyranosyl-(1→3)-2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-Dglucopyranoside (9), was achieved from building block derivatives of the component mono- and disaccharide units. Initially the benzyl lactoside acceptor 3, which has a free hydroxyl group at position O-3`, was prepared via selective opening

  三糖苄基2-乙酰氨基-3,6-二-O-苄基-2-脱氧-β-D-吡喃葡萄糖基-（1→3）-2,4,6-三-O-苄基-β-D-的合成半乳糖吡喃糖基-（1→4）-2,3,6-三-O-苄基-β-D-吡喃吡喃糖苷（9）是由单糖和二糖单元的结构单元衍生物制得的。最初，通过选择性地打开3'，4'-环原酸酯衍生物2制备在O-3'位置具有游离羟基的苄基乳糖苷受体3。糖胺基供体2-甲基（3,4，将6-三-O-乙酰基-1,2-二脱氧-（α-D-吡喃吡喃）-[2`，1`：4,5] -2-恶唑啉（4）与3偶联，得到三糖苷5依次进行8-脱O-乙酰化（5→6），苄基化（6→7），苄基化（7→8）和还原性打开亚苄基乙缩醛功能得到目标三糖9，
• Chemo-enzymatic synthesis of a tetra- and octasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 14
  作者：John A.F Joosten、Johannis P Kamerling、Johannes F.G Vliegenthart

  DOI：10.1016/s0008-6215(03)00313-6

  日期：2003.11

  tetrasaccharide repeating units of Streptococcus pneumoniae serotype 14 capsular polysaccharide. In a chemical approach, the intermediate linear trisaccharide 3 and hexasaccharide 4 were synthesized. Galactose residues were beta-(1-->4)-connected to the internal N-acetyl-beta-D-glucosamine residues by using bovine milk beta-1,4-galactosyltransferase. Both title oligosaccharides will be conjugated to carrier proteins

  化学酶合成描述了四糖β-D-Galp-（1-> 4）-β-D-Glcp-（1-> 6）-β-D-Galp-（1-> 4 ）]-beta-D-GlcpNAc-（1-> O（CH（2））（6）NH（2）（1）和八糖beta-D-Galp-（1-> 4）-beta-D -Glcp-（1-> 6）-[beta-D-Galp-（1-> 4）]-beta-D-GlcpNAc-（1-> 3）-beta-D-Galp-（1- -> 4）-beta-D-Glcp-（1-> 6）-[beta-D-Galp-（1-> 4）]-beta-D-GlcpNAc-（1-> O（CH（ 2））（6）NH（2）（2），分别代表肺炎链球菌血清型14荚膜多糖的一个和两个四糖重复单元，化学合成了中间体线性三糖3和六糖4，半乳糖残基为β-使用牛乳β-1,4-半乳糖基转移酶将（1-> 4）连接到内部N-乙酰基-β-D-葡萄糖胺残基。
• Lay, Luigi; Manzoni, Leonardo; Schmidt, Richard R., Carbohydrate Research, 1998, vol. 310, # 3, p. 159 - 172
  作者：Lay, Luigi、Manzoni, Leonardo、Schmidt, Richard R.

  DOI：——

  日期：——
• N,N-Diacetyl-Glucosamine and -Galactosamine Derivatives as Glycosyl Donors
  作者：J Castro-Palomino

  DOI：10.1016/00404-0399(50)14068-

  日期：1995.9.18

  N-Acetyl-glucosamine and N-acetyl-galactosamine were converted into the O-acetyl protected 1-methylthio-derivatives 1A,B which were then transformed into N,N-diacetyl derivatives 2A and 2B, respectively. Activation of 2A,B with DMTST afforded good glycosyl donors for the generation of P-linkages: thus, reaction with accepters 3a,b gave oligosaccharides 4Aa and 4Ba in high and 4Ab and 4Bb in good yields. Mono-N-deacetylation could be performed with NaOMe/MeOH in quantitative yield, thus concluding a convenient procedure for the formation of beta-linked GlcNAc and GalNAc glycosides.