methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 118579-76-3

分子结构分类

有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物

中文名称

——

中文别名

——

英文名称

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

英文别名

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

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

CAS

118579-76-3

化学式

C₆₂H₅₈O₁₅

mdl

——

分子量

1043.13

InChiKey

FDLUWVJPROUMHG-ZQGVGXTDSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.33±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

10.3
重原子数：

77
可旋转键数：

26
环数：

9.0
sp3杂化的碳原子比例：

0.26
拓扑面积：

170
氢给体数：

0
氢受体数：

15

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
——	2,3,4,6-tetra-O-benzoyl-D-glucopyranose	627466-64-2	C₃₄H₂₈O₁₀	596.59
2,3,4,6-四-O-苯甲酰基-D-吡喃葡萄糖	2,3,4,6-tetra-O-benzoyl-β-D-glucopyranose	64768-20-3	C₃₄H₂₈O₁₀	596.59
——	[(2R,3R,4S,5R)-3,4,5-tribenzoyloxy-6-pent-4-enoyloxyoxan-2-yl]methyl benzoate	920749-30-0	C₃₉H₃₄O₁₁	678.692
2,3,4,6-四-O-苯甲酰基葡萄糖三氯乙酰亚胺酯	2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate	151767-11-2	C₃₆H₂₈Cl₃NO₁₀	740.978
甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷	methyl 2,3,4-tri-O-benzyl-D-glucopyranoside	53008-65-4	C₂₈H₃₂O₆	464.558
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
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-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside	——	C₂₈H₃₀O₆	462.543
——	2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl diethyl phosphite	——	C₃₈H₃₇O₁₂P	716.678
——	[(2S,3aR,5R,6R,7S,7aR)-6,7-dibenzoyloxy-2-phenyl-2-prop-2-ynoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl benzoate	953795-81-8	C₃₇H₃₀O₁₀	634.639
——	perbenzoyl-D-glucopyranosyl o-(1-hexynyl)benzoate	1221151-98-9	C₄₇H₄₀O₁₁	780.828
——	4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside	3162-96-7	C₁₄H₁₈O₆	282.293
——	methyl 2,3,6-tri-O-benzyl-4-O-trimethylsilyl-α-D-glucopyranoside	91298-42-9	C₃₁H₄₀O₆Si	536.74
β-D-葡萄糖五乙酸酯	β-D-glucose pentaacetate	604-69-3	C₁₆H₂₂O₁₁	390.344
——	[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[bis(dimethylamino)phosphoryloxy]oxan-2-yl]methyl benzoate	143520-21-2	C₃₈H₃₉N₂O₁₁P	730.708
——	2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl fluoride	4163-40-0	C₃₄H₂₇FO₉	598.581
——	2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl fluoride	4163-39-7	C₃₄H₂₇FO₉	598.581
——	2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl p-trifluoromethylbenzylthio-p-trifluoromethylphenyl formimidate	——	C₅₀H₃₇F₆NO₁₀S	957.901
——	2,3,4,6-tetra-O-benzoylglucosyl bromide	14218-11-2	C₃₄H₂₇BrO₉	659.487
——	2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl bromide	165877-99-6	C₃₄H₂₇BrO₉	659.487
——	methyl tetra-O-benzoyl-1-thio-β-D-glucopyranoside	104707-00-8	C₃₅H₃₀O₉S	626.684
——	ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside	——	C₃₆H₃₂O₉S	640.711
——	dodecyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside	275817-34-0	C₄₆H₅₂O₉S	780.979
——	stearyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside	275817-35-1	C₅₂H₆₄O₉S	865.141
——	phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside	62774-33-8	C₄₀H₃₂O₉S	688.755
alpha-甲基葡萄糖甙	methyl-alpha-D-glucopyranoside	97-30-3	C₇H₁₄O₆	194.185
——	p-tolyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside	172847-85-7	C₄₁H₃₄O₉S	702.782

反应信息

作为产物：

描述：

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在吡啶、甲醇、 lithium tetrafluoroborate 、 3 A molecular sieve 、 sodium methylate 作用下，以乙腈为溶剂，反应 15.0h，生成 methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

参考文献：

名称：

由苯基或乙基1-硫代糖苷电合成二糖

摘要：

糖基供体苯基和乙基2,3,4,6-四-O-苄基-1-硫代-β-D-吡喃葡萄糖苷在干燥的乙腈中在各种伯和仲糖醇的存在下进行恒流电解未分裂的细胞，以良好的产率选择性地产生了β-连接的二糖衍生物。苯基2,3,4,6-四-O-苯甲酰基-1-硫代-β-D-吡喃葡萄糖苷以良好至中等的产率专门提供了β-葡萄糖苷。

DOI：

10.1016/0008-6215(83)85004-6

点击查看最新优质反应信息

文献信息

Gold(I)-Catalyzed Glycosylation with Glycosyl Ynenoates as Donors

作者：Xiaona Li、Chenyu Li、Rongkun Liu、Jiazhe Wang、Zixuan Wang、Yan Chen、You Yang

DOI：10.1021/acs.orglett.9b03851

日期：2019.12.6

A simple and versatile glycosylation method with both armed and disarmed glycosyl ynenoates as donors is developed. Employing a gold(I) complex as catalyst with or without the assistance of TfOH, the scope of the present glycosylation protocol is very wide. The utility of the present ynenoate donors is demonstrated in the efficient synthesis of oligosaccharides via the latent-active strategy and the

开发了一种简单且通用的糖基化方法，其中武装和解除武装的糖基炔诺酸酯都作为供体。在有或没有TfOH的辅助下采用金（I）配合物作为催化剂，本糖基化方案的范围非常宽。通过潜在的活性策略和多重正交一锅策略在低聚糖的有效合成中证明了本发明的炔酸供体的实用性。最后，该方法能够正式合成肺炎链球菌血清型3的四糖半抗原和32mer聚甘露糖苷的高度收敛合成。
An efficient construction of 1,2-trans-β-glycosidic linkages capitalizing on glycopyranosyl N,N,N′,N′-tetramethylphosphroamidates as shelf-stable glycosyl donors

作者：Shun-ichi Hashimoto、Yuki Yanagiya、Takeshi Honda、Hideki Harada、Shiro Ikegami

DOI：10.1016/s0040-4039(00)92679-0

日期：1992.6

stereocontrolled 1,2-trans-β-glycosidation reaction with or without neighbouring group participation has been developed by using benzyl- or benzoyl-protected glycopyranosyl N,N,N',N'-tetramethylphosphoroamidates as shelf-stable glycosyl donors in the presence of trimethylsilyl trifluoromethanesulfonate or boron trifluoride etherate. Several notable features of the present method not observed with the diphenyl

通过使用苄基或苯甲酰基保护的吡喃葡萄糖基N，N，N'，N'-四甲基磷酰胺基酸酯作为在货架上稳定的糖基供体，已经开发了具有或不具有邻近基团参与的高度立体控制的1,2-反式-β-糖苷化反应。存在三甲基甲硅烷基三氟甲磺酸盐或三氟化硼醚化物。还描述了用磷酸二苯酯法未观察到的本方法的几个显着特征。
Acid-Catalyzed <i>O</i>-Glycosylation with Stable Thioglycoside Donors

作者：Kristina D. Lacey、Rashanique D. Quarels、Shaofu Du、Ashley Fulton、Nicholas J. Reid、Austin Firesheets、Justin R. Ragains

DOI：10.1021/acs.orglett.8b02125

日期：2018.9.7

4-(4-methoxyphenyl)-4-pentenylthioglycosides (MPTGs), undergo acid-catalyzed O-glycosylations with a range of sugar and nonsugar alcohols at 25 °C. Electron density at the styrene alkene is critical for reactivity while sugar protecting group patterns have a minimal effect. In contrast with most methods for thioglycoside activation, acid-catalyzed activation of MBTGs is compatible with electroneutral alkenes

两类硫代糖苷（4-（4-甲氧基苯基）-3-丁烯基硫代糖苷（MBTG）和4-（4-甲氧基苯基）-4-戊烯基硫代糖苷（MPTG））经过酸催化的O-糖基化反应，并带有一系列糖和非糖醇在25°C下。苯乙烯烯烃上的电子密度对于反应性至关重要，而糖保护基的作用则微乎其微。与大多数硫糖苷活化方法相反，MBTG的酸催化活化与电子中性烯烃相容。
An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf

作者：Yao Li、You Yang、Biao Yu

DOI：10.1016/j.tetlet.2008.04.017

日期：2008.5

A new and powerful glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors and Ph3PAuOTf as a promoter is disclosed. The donors are readily available and stable; the glycosidic coupling yields are generally excellent; the promotion system is catalytic, neutral, and orthogonal to the known glycosylation conditions.

公开了一种新的且功能强大的糖基化方案，其中糖基邻炔基苯甲酸酯为供体，Ph 3 PAuOTf为启动子。捐助者随时可用且稳定；糖苷偶联的产量通常是优异的；促进系统是催化的，中性的，并且与已知的糖基化条件正交。
Gold(I)-Catalyzed Glycosylation with Glycosyl<i>ortho</i>-Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin

作者：Yao Li、Xiaoyu Yang、Yunpeng Liu、Cunsheng Zhu、You Yang、Biao Yu

DOI：10.1002/chem.200902548

日期：2010.2.8

coupling with the poorly nucleophilic amides gives satisfactory yields. Moreover, excellent α‐selective glycosylation with a 2‐deoxy sugar donor and β‐selective sialylation have been realized. Application of the present glycosylation protocol in the efficient synthesis of a cyclic triterpene tetrasaccharide have further demonstrated the versatility and efficacy of this new method, in that a novel chemoselective

糖基邻炔基苯甲酸酯已成为在金（I）配合物如Ph 3 PAuOTf和Ph 3 PAuNTf 2催化下进行糖苷化的新一代供体（Tf ＝三氟甲磺酸盐）。这些供体种类繁多，包括2-脱氧糖和唾液酸供体，易于制备且易于保存。与醇类的糖苷偶联收率通常非常好；即使与不良亲核酰胺直接偶联也能获得令人满意的收率。此外，已经实现了具有2-脱氧糖供体的出色的α-选择性糖基化和β-选择性唾液酸化。本糖基化方案在环状三萜四糖高效合成中的应用进一步证明了这种新方法的多功能性和有效性，因为已实现了羧酸的新型化学选择性糖基化和新的单锅顺序糖基化序列。