methyl α-D-glucopyranosyl-(1->4)-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-D-glucopyranosyl-(1->4)-α-D-galactopyranoside
• 英文别名: Glc(a1-4)a-Gal1Me；(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: FHNIYFZSHCGBPP-NCQZQJBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  Α-D-乳酸吡喃糖苷甲酯	methyl α-D-galactopyranoside	3396-99-4	C7H14O6	194.185
  蔗糖	Sucrose	57-50-1	C12H22O11	342.3
  ——	methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-galactopyranoside	348631-15-2	C55H58O11	895.059

反应信息

• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-galactopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以91%的产率得到methyl α-D-glucopyranosyl-(1->4)-α-D-galactopyranoside
  参考文献：
  名称：

  甲基α-d-吡喃葡萄糖基-（1→4）-α-d-吡喃半乳糖苷和甲基α-d-二甲苯基-己基-4-氟吡喃糖基-（1→4）-α-d-吡喃半乳糖苷的合成

  摘要：

  摘要甲基α-d-吡喃葡萄糖基-（1→4）-α-d-吡喃半乳糖苷（1）和甲基α-d-木糖己基-4-氟吡喃糖基-（1→4）-α-d-吡喃半乳糖苷的合成（4）报道。酮二糖4在我们设计，合成和研究果胶酸裂合酶抑制剂中很重要。合成的关键步骤是高产立体定向形成甲基4,6-O-亚苄基-2'，3'-二-O-苄基-α-d-吡喃葡萄糖基-（1→4）-2， 3，6-三-O-苄基-α-d-吡喃半乳糖苷（15），其通过使2，3-二-O-苄基-4，6-O-亚苄基-d-吡喃葡萄糖基三氯乙酰亚氨酸酯（10）与在催化量的叔丁基二甲基甲硅烷基三氟甲烷磺酸盐（TMSOTF）存在下，合成2,3,6-三-O-苄基-α-d-吡喃半乳糖苷（14）。将化合物15水解生成二糖1或用NaBH3CN-HCl的1：1个四氢呋喃-醚，生成甲基2,3,6-三-O-苄基-α-d-吡喃葡萄糖基-（1→4）-2,3,6-三-O-苄基-α-d-吡喃半乳糖苷（2

  DOI：

  10.1016/s0008-6215(01)00044-1

文献信息

• Alternansucrase acceptor reactions with methyl hexopyranosides
  作者：Gregory L. Côté、Christopher A. Dunlap

  DOI：10.1016/s0008-6215(03)00324-0

  日期：2003.9

  pyranoside and methyl alpha-D-glucopyranosyl-(1-->4)-alpha-D-galactopyranoside, in a 2.5:1 molar ratio. Methyl D-allopyranosides were glucosylated primarily at position 6, yielding methyl alpha-D-glucopyranosyl-(1-->6)-D-allopyranosides. The latter subsequently gave rise to methyl alpha-D-glucopyranosyl-(1-->6)-alpha-D-glucopyranosyl-(1-->6)-D-allopyranosides. In general, the methyl alpha-D-hexopyranosides

  交替糖（EC 2.4.1.140，蔗糖：（1-> 6），（1-> 3）-α-D-葡聚糖6（3）-α-D-葡糖基转移酶）是一种D-葡聚糖酶，可合成来自蔗糖的与α-（1-> 3），（1-> 6）连接的D-葡聚糖。它还通过D-吡喃葡萄糖基转移到各种受体糖上来合成寡糖。我们已经研究了甲基糖苷作为模型化合物产生的受体产物，以便更好地了解交替糖蔗糖受体反应的特异性。由甲基β-D-吡喃葡糖苷产生的初始产物是甲基β-异麦芽糖苷，随后对其进行糖基化以生成甲基β-异麦芽三糖苷和甲基α-D-吡喃葡糖基-（1→3）-α-D-吡喃葡糖基-（ 1-> 6）-β-D-吡喃葡萄糖苷。这些产物类似于先前从甲基α-D-吡喃葡萄糖苷描述的那些。来自甲基α-D-甘露吡喃糖苷的主要初始受体产物是甲基α-D-吡喃葡萄糖基-（1→6）-α-D-甘露吡喃糖苷，但也分离并表征了一些次要产物，包括3,6-二-O-取代的甘露吡喃糖苷。甲基α-
• Efficient Intramolecular Glycosylation Supported by a Rigid Spacer
  作者：Matthias Müller、Ursula Huchel、Armin Geyer、Richard R. Schmidt

  DOI：10.1021/jo990132e

  日期：1999.8.1

  The m-xylylene moiety was employed as rigid spacer in intramolecular glycoside bond formation. Fifteen-membered macrocycle formation starting from 6-O-linked donor and 6- and 4-O-linked acceptor (5a,b, 6b) led exclusively to beta(1-4)- and beta(1-6)-linked compounds 7 beta and 8 beta, respectively, which gave cellobioside and gentiobioside derivatives. The glycosylation yields could be improved by 14-membered macrocycle formation. In the four cases studied, the donor was 6-O-linked to the spacer. For the acceptor linkage to the spacer and the accepting hydroxy group, relative D-/L-threo- and D-/L-erythro-arrangements were chosen. Standard glycosylation conditions led in three cases (13, 14, 23) only to beta-linkage in high yield (16 beta, 17 beta, 25 beta). For the transformation of 24, having a D-erythro-arrangement in the acceptor moiety, the alpha-anomer 26 alpha was preferentially obtained. Limitation of the conformational space of the donor and the acceptor as in 31, which is stereochemically identical with 24, led to the corresponding alpha-glycoside 32 alpha in 87% yield. Synthesis of a pseudo mirror image of 23 [having 6-(D)/3-(D-threo)-arrangement], namely 35, having 3(L)/6-(L-threo)-arrangement of the donor and acceptor moieties, expectedly gave only alpha-glycoside 36 alpha in very high yield. Thus, the efficiency and versatility of this conceptual approach to intramolecular glycoside bond formation is exhibited.
• BAUMANN, HERBERT;ERBING, BERTIL;JANSSON, PER-ERIK;KENNE, LENNART, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N2, C. 2145-2151
  作者：BAUMANN, HERBERT、ERBING, BERTIL、JANSSON, PER-ERIK、KENNE, LENNART

  DOI：——

  日期：——
• Synthesis of methyl α-d-glucopyranosyl-(1→4)-α-d-galactopyranoside and methyl α-d-xylo-hex-4-ulopyranosyl-(1→4)-α-d-galactopyranoside
  作者：Louis J. Liotta、Rita D. Capotosto、Rachel A. Garbitt、Brian M. Horan、Pamela J. Kelly、Andrew P. Koleros、Lisa M. Brouillette、Amy M. Kuhn、Sonia Targontsidis

  DOI：10.1016/s0008-6215(01)00044-1

  日期：2001.4

  -glucopyranosyl-(1→4)-α- d -galactopyranoside (1) and methyl α- d -xylo-hex-4-ulopyranosyl-(1→4)-α- d -galactopyranoside (4) are reported. The keto-disaccharide 4 is of interest in our design, synthesis, and study of pectate lyase inhibitors. The key step in the syntheses was the high-yielding, stereospecific formation of methyl 4,6-O-benzylidene-2′,3′-di-O-benzyl-α- d -glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-

  摘要甲基α-d-吡喃葡萄糖基-（1→4）-α-d-吡喃半乳糖苷（1）和甲基α-d-木糖己基-4-氟吡喃糖基-（1→4）-α-d-吡喃半乳糖苷的合成（4）报道。酮二糖4在我们设计，合成和研究果胶酸裂合酶抑制剂中很重要。合成的关键步骤是高产立体定向形成甲基4,6-O-亚苄基-2'，3'-二-O-苄基-α-d-吡喃葡萄糖基-（1→4）-2， 3，6-三-O-苄基-α-d-吡喃半乳糖苷（15），其通过使2，3-二-O-苄基-4，6-O-亚苄基-d-吡喃葡萄糖基三氯乙酰亚氨酸酯（10）与在催化量的叔丁基二甲基甲硅烷基三氟甲烷磺酸盐（TMSOTF）存在下，合成2,3,6-三-O-苄基-α-d-吡喃半乳糖苷（14）。将化合物15水解生成二糖1或用NaBH3CN-HCl的1：1个四氢呋喃-醚，生成甲基2,3,6-三-O-苄基-α-d-吡喃葡萄糖基-（1→4）-2,3,6-三-O-苄基-α-d-吡喃半乳糖苷（2