methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside | 77117-44-3

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside

英文别名

methyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside；methyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside；methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1Me；(2S,3R,4S,5R,6R)-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside化学式

CAS

77117-44-3

化学式

C₆₂H₆₆O₁₁

mdl

——

分子量

987.199

InChiKey

XGUQGDPCAPRZDC-WWBLMGCDSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

83-85 °C
密度：

1.23±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

9.5
重原子数：

73
可旋转键数：

26
环数：

9.0
sp3杂化的碳原子比例：

0.32
拓扑面积：

102
氢给体数：

0
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
甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷	methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside	19488-48-3	C₂₈H₃₂O₆	464.558
——	(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol	——	C₂₈H₃₂O₆	464.558
——	2-allyloxy-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran	6207-45-0	C₃₇H₄₀O₆	580.721
2,3,4,6-四苄基-D-吡喃葡萄糖	2,3,4,6-Tetra-O-benzyl-D-glucopyranose	4132-28-9	C₃₄H₃₆O₆	540.656
——	methyl 2,3,6-tri-O-benzyl-4-O-isopropenyl-α-D-glucopyranoside	139608-10-9	C₃₁H₃₆O₆	504.623
——	methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside	——	C₂₈H₃₀O₆	462.543
——	methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside	——	C₂₈H₃₀O₆	462.543
甲基-4,6-O-亚苄基-Α-D-吡喃葡糖苷	methyl 4,6-O-benzylidene-α-D-glucopyranoside	3162-96-7	C₁₄H₁₈O₆	282.293
——	[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] pent-4-enoate	920749-29-7	C₃₉H₄₂O₇	622.758
——	isopropenyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranosyl carbonate	139608-01-8	C₃₈H₄₀O₈	624.731
2,3,4,6-四-O-苯基-Alpha-D-吡喃葡萄糖基三氯乙酰亚氨酸	2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate	74808-09-6	C₃₆H₃₆Cl₃NO₆	685.044
——	2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate	132201-75-3	C₃₆H₃₆Cl₃NO₆	685.044
——	2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate	90357-89-4	C₃₆H₃₆Cl₃NO₆	685.044
——	methyl 2,3,6-tri-O-benzyl-4-O-trimethylsilyl-α-D-glucopyranoside	91298-42-9	C₃₁H₄₀O₆Si	536.74
——	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl diethyl phosphite	193953-69-4	C₃₈H₄₅O₈P	660.744
——	diethylphosphoryl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside	79386-47-3	C₃₈H₄₅O₉P	676.744
——	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl N-trichloroacetylcarbamate	——	C₃₇H₃₆Cl₃NO₈	729.054
——	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl N-phenyltrifluoroacetimidate	339276-14-1	C₄₂H₄₀F₃NO₆	711.778
——	2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate	96863-21-7	C₃₆H₄₁O₆PS	632.758
——	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl benzyl phthalate	——	C₄₉H₄₆O₉	778.899
β-D-葡萄糖五乙酸酯	β-D-glucose pentaacetate	604-69-3	C₁₆H₂₂O₁₁	390.344
1,2,3,4,6-D-葡萄糖五乙酸酯	D-galactose pentaacetate	25878-60-8	C₁₆H₂₂O₁₁	390.344
alpha-甲基葡萄糖甙	methyl-alpha-D-glucopyranoside	97-30-3	C₇H₁₄O₆	194.185
——	N-[ethoxy-[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyphosphanyl]-N-propan-2-ylpropan-2-amine	205814-21-7	C₄₂H₅₄NO₇P	715.867
2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖酰氟	2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride	78153-79-4	C₃₄H₃₅FO₅	542.647
2,3,4,6-四-O-苄基-D-吡喃葡萄糖酰氟	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride	122741-44-0	C₃₄H₃₅FO₅	542.647
2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖酰氟	2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride	89025-46-7	C₃₄H₃₅FO₅	542.647
——	6-chloro-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)pyridazine	210777-67-6	C₃₈H₃₇ClN₂O₆	653.175
氯 2,3,4,6-四-O-苄基-\|á-D-吡喃葡萄糖苷	tetra-O-benzyl glucopyranosyl chloride	25320-59-6	C₃₄H₃₅ClO₅	559.102
——	diphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucosyl phosphate	79386-43-9	C₄₆H₄₅O₉P	772.832
(2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃	2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide	4196-35-4	C₃₄H₃₅BrO₅	603.553
——	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl bromide	67773-43-7	C₃₄H₃₅BrO₅	603.553
——	2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl [p-(trifluoromethyl)benzyl]thio-N-[p-(trifluoromethyl)phenyl]formimidate	——	C₅₀H₄₅F₆NO₆S	901.967
D-吡喃葡萄糖	D-Galactose	10257-28-0	C₆H₁₂O₆	180.158

反应信息

作为产物：

描述：

β-D-葡萄糖五乙酸酯在 N-碘代丁二酰亚胺、三氟甲磺酸、 4 A molecular sieve 、三氟化硼乙醚、 sodium hydride 作用下，以四氢呋喃、 1,2-二氯乙烷、 N,N-二甲基甲酰胺、乙腈为溶剂，反应 0.83h，生成 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside

参考文献：

名称：

Lauryl and Stearyl Thioglycosides: Preparation and Reactivity of the Glycosyl Donor

摘要：

月桂醇和硬脂醇硫糖苷是通过路易斯酸催化的反应制备的，该反应涉及1-O-乙酰化糖与非挥发性和几乎无气味的壬基硫醇和十八烷硫醇。将这些硫糖苷用N-碘琥珀酰亚胺-TfOH激活，生成优良产率的二糖供体。

DOI：

10.1246/cl.2000.326

点击查看最新优质反应信息

文献信息

Blue Light Photocatalytic Glycosylation without Electrophilic Additives

作者：Peng Wen、David Crich

DOI：10.1021/acs.orglett.7b00932

日期：2017.5.5

employing stable and readily accessible O-glycosyl derivatives of 2,2,6,6-tetramethylpiperidin-1-ol is presented that employs an iridium-based photocatalyst and blue LEDs. The reaction proceeds at room temperature and in the absence of additives other than 4 Å molecular sieves. Stereoselectivities are modest but nevertheless dependent on the anomeric configuration of the donor, suggesting a substantial

提出了使用2,2,6,6-四甲基哌啶-1-醇的稳定且易于获得的O-糖基衍生物进行糖苷键的光催化形成，该衍生物使用基于铱的光催化剂和蓝色LED。该反应在室温下且在没有4Å分子筛以外的添加剂的情况下进行。立体选择性是适度的，但是取决于供体的异头构型，这表明相当大程度的一致特征。
AuCl3- and AuCl3-Phenylacetylene-Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates

作者：Rashmi Roy、Ashok Kumar Palanivel、Asadulla Mallick、Yashwant D. Vankar

DOI：10.1002/ejoc.201500137

日期：2015.6

obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature.

通过使用 AuCl3-苯乙炔中继催化剂体系进行武装和解除武装的三氯乙酰亚胺基糖基供体的糖基化。该催化体系的有效性也与单独使用 AuCl3 作为催化剂的有效性进行了比较。使用这些催化剂的糖基化在室温下在 5-45 分钟内有效进行。2-O-乙酰保护的去武装糖基供体的糖基化获得了优异的非对映选择性，而武装糖基三氯乙酰亚胺产生了异头糖苷的混合物。酸敏感性亲核试剂，如 Fmoc-丝氨酸叔丁酯或 Fmoc-苏氨酸叔丁酯，在室温温和条件下成功地进行了糖基化，尽管产率适中。
O-Glycosylation Enabled by N-(Glycosyloxy)acetamides

作者：Miao Liu、Bo-Han Li、De-Cai Xiong、Xin-Shan Ye

DOI：10.1021/acs.joc.8b01003

日期：2018.8.3

A novel glycosylation protocol has been established by using N-(glycosyloxy)acetamides as glycosyl donors. The N-oxyacetamide leaving group in donors could be rapidly activated in the presence of Cu(OTf)2 or SnCl4 under microwave irradiation. This glycosylation process afforded the coupled products in high yields, and the reaction enjoyed a broad substrate scope, even for disarmed donors and hindered

通过使用N-（糖基氧基）乙酰胺作为糖基供体已经建立了新的糖基化方案。在微波辐射下，存在Cu（OTf）2或SnCl 4的情况下，供体中的N-氧乙酰胺离去基团可以快速活化。该糖基化过程以高收率提供了偶联产物，并且该反应享有广泛的底物范围，即使对于缴械的供体和受阻的受体也是如此。供体的容易获得，N-（糖基氧基）乙酰胺的高稳定性以及小的离去基团使该方法非常实用。
Iron(<scp>iii</scp>) chloride modulated selective 1,2-trans glycosylation based on glycosyl trichloroacetimidate donors and its application in orthogonal glycosylation

作者：Mana Mohan Mukherjee、Nabamita Basu、Rina Ghosh

DOI：10.1039/c6ra21859h

日期：——

FeCl3 can also modulate the 1,2-trans selectivity of the reaction of 2-O-alkylated gluco- and galacto-pyranosyl trichloroacetimidates with phenolic compounds leading to the generation of the corresponding β-O-aryl glycosides in excellent yield and selectivity. Apart from these the present methodology has been successfully utilized for double glycosylation and orthogonal glycosylation reactions along

人们已经集中研究了一种新的糖基化方法，该方法可从10摩尔％的FeCl 3介导的相应的三氯乙酰亚氨酸酯供体有效立体选择性合成β-葡萄糖和半乳糖苷。FeCl 3也已应用于许多基于葡萄糖，半乳糖，甘露糖和鼠李糖的三氯乙酰亚氨酸酯供体，这些供体在C-2位置掺入了各种保护基，从而制备了多种具有优异的1,2-反式选择性的二糖和三糖。FeCl 3还可调节2- O反应的1,2-反式选择性-烷基化的葡糖基和半乳糖基-吡喃糖基三氯乙酰亚胺酸酯与酚类化合物的结合，可导致以优异的产率和选择性生成相应的β- O-芳基糖苷。除此之外，本方法已成功地用于双糖基化和正交糖基化反应，以及在三锅合成的一锅三组分正交糖基化反应中的应用。
A “Traceless” Directing Group Enables Catalytic SN2 Glycosylation toward 1,2-cis-Glycopyranosides

作者：Xu Ma、Zhitong Zheng、Yue Fu、Xijun Zhu、Peng Liu、Liming Zhang

DOI：10.1021/jacs.1c04584

日期：2021.8.11

Generally applicable and stereoselective formation of 1,2-cis-glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2-trans glycosyl ester donors. This SN2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a

1,2-顺式-吡喃糖苷键的普遍适用和立体选择性形成仍然是碳水化合物化学中长期追求但尚未实现的目标。这项工作通过在 1,2-反式糖基酯供体的异头位置上的立体倒置推进了应对这一挑战的策略。这种 S N 2 糖基化是在金催化下通过以恶唑为基础的导向基团实现的，该导向基团最佳地束缚在离去基团上，并在温和的催化条件下以大多数优异的产率和良好的选择性实现。该策略也适用于寡糖的合成。