methyl 2,3-di-O-benzyl-α-D-altropyranoside | 33164-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-α-D-altropyranoside
• 英文别名: Methyl-2,3-di-O-benzyl-α-D-altropyranosid；(2R,3R,4R,5S,6S)-2-(hydroxymethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 33164-03-3
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: AOHYQGVMTDLXSL-XKRYSZRTSA-N

物化性质

• 沸点：
  537.1±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-α-D-altropyranoside 在 钯 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium hydrogen telluride 、 氢气 、 叠氮化四丁基铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3R,4S,5R)-2-甲基-3,4,5-哌啶三醇
  参考文献：
  名称：

  Synthesis fromD-glucose of 1,5-dideoxy-1,5-imino-L-fucitol, a potent α-L-fucosidase inhibitor

  摘要：

  1,5-二脱氧-1,5-亚氨基-L-岩藻糖醇（1），由甲基α-D-吡喃葡萄糖苷合成，是一种强效的竞争性抑制剂，能够抑制α-L-岩藻糖苷酶（如牛附睾中的）催化对硝基苯α-L-岩藻糖苷的水解，在2.5×10⁻⁸M浓度下导致酶活性的50%抑制。

  DOI：

  10.1039/c39850000841
• 作为产物：
  描述：

  (4aR,6S,7S,8S,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 在 氢氧化钾 、 碘 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 methyl 2,3-di-O-benzyl-α-D-altropyranoside
  参考文献：
  名称：

  Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine in Place ofN-Acetyl Glucosamine

  摘要：

  The synthesis of the new sialyl Lewis X analogue, 4-O-(alpha-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-beta-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-alpha-D-altropyranoside sugar precursor 10 using the Ganem/Bernotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.

  DOI：

  10.1080/07328300008544095

文献信息

• Synthesis of 2-Acetoxy-4-formylphenyl 2,3-Di-<i>O</i>-acetyl-6-deoxy-β-D-arabino-5-hexulofuranoside, Structure Confirmation of the Anomeric Configuration of Antibiotic Hygromycin A
  作者：Noritaka Chida、Masami Ohtsuka、Seiichiro Ogawa

  DOI：10.1246/cl.1988.969

  日期：1988.6.5

  2-Acetoxy-4-formylphenyl 2,3-di-O-acetyl-6-deoxy-β-D-arabino-5-hexulofuranoside, one of the degradation products of antibiotic hygromycin A, was synthesized. The present study confirmed the anomeric configuration of the antibiotic to be “β”.

  合成了 2-Acetoxy-4-formylphenyl 2,3-di-O-acetyl-6-deoxy-β-D-arabino-5-hexulofuranoside，它是抗生素潮霉素 A 的降解产物之一。本研究证实抗生素的异头构型为“β”。
• Regioselective de-O-benzylation of phenylsulfonylethylidene (PSE) acetals-containing benzylated monosaccharides using triisobutylaluminum (TIBAL)
  作者：Bérengère Chevalier-du Roizel、Elena Cabianca、Patrick Rollin、Pierre Sinaÿ

  DOI：10.1016/s0040-4020(02)01249-8

  日期：2002.11

  A series of benzylated monosaccharidic PSE acetals undergoes regioselective TIBAL-mediated de-O-benzylation, to afford monobenzyl ethers, readily available as building blocks for oligosaccharides synthesis.

  一系列苄基化的单糖化PSE缩醛经过区域选择性TIBAL介导的去-O-苄基化反应，得到单苄基醚，很容易用作寡糖合成的基础。
• The use of pyridinium chlorochromate for preparation of hexopyranosiduloses without epimerisation
  作者：Brian B. Bissember、Richard H. Wightman

  DOI：10.1016/s0008-6215(00)85688-8

  日期：1980.5
• Total synthesis of antibiotic hygromycin A
  作者：Noritaka Chida、Masami Ohtsuka、Keiichi Nakazawa、Seiichiro Ogawa

  DOI：10.1021/jo00009a009

  日期：1991.4

  The first total synthesis of the antibiotic (-)-hygromycin A (1) has been achieved by a coupling reaction of the sugar moiety (2) and the cyclitol moiety (3). Both components were synthesized in homochiral forms starting from D-glucose. This synthesis fully confirmed the unique structure of 1, which is much different from other usual aminocyclitol antibiotics.
• CHIDA, NORITAKA;OHTSUKA, MASAMI;NAKAZAWA, KEIICHI;OGAWA, SEIICHIRO, J. ORG. CHEM., 56,(1991) N, C. 2976-2983
  作者：CHIDA, NORITAKA、OHTSUKA, MASAMI、NAKAZAWA, KEIICHI、OGAWA, SEIICHIRO

  DOI：——

  日期：——