2,3,4,2',3',4',6'-hepta-O-acetyl-α-D-isomaltosyl bromide | 81129-75-1

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

2,3,4,2',3',4',6'-hepta-O-acetyl-α-D-isomaltosyl bromide

英文别名

Glc2Ac3Ac4Ac6Ac(a1-6)a-Glc1Br2Ac3Ac4Ac；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methoxy]oxan-2-yl]methyl acetate

2,3,4,2',3',4',6'-hepta-O-acetyl-α-D-isomaltosyl bromide化学式

CAS

81129-75-1

化学式

C₂₆H₃₅BrO₁₇

mdl

——

分子量

699.458

InChiKey

QLNKYWGJSVLWHY-VRECAULFSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

644.7±55.0 °C(Predicted)
密度：

1.47±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

0.2
重原子数：

44
可旋转键数：

18
环数：

2.0
sp3杂化的碳原子比例：

0.73
拓扑面积：

212
氢给体数：

0
氢受体数：

17

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
——	β-isomaltose octaacetate	4627-41-2	C₂₈H₃₈O₁₉	678.598
——	O-(α-D-glucopyranosyl)-(1<*>6)-O-1,2,3,4-tetra-O-cetyl-β-D-glucopyranose	80977-04-4	C₂₀H₃₀O₁₅	510.449

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside	136310-58-2	C₂₉H₄₀O₁₈	676.626
——	O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<>6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1<>6)-1,2,3,4-tetra-O-acetyl-β-D-glucopyranose	81025-65-2	C₄₀H₅₄O₂₇	966.853
——	O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1[]6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1[]6)-2,3,4-tri-O-acetyl-α-D-glucopyranosylamine	80977-06-6	C₃₈H₅₃NO₂₅	923.831
——	O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<>6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1<>6)-2,3,4-tri-O-acetyl-β-D-glucopyranosylamine	80977-07-7	C₃₈H₅₃NO₂₅	923.831
——	2,5-anhydro-3-O-(β-gentiobiosyl)-D-mannitol	862607-74-7	C₁₈H₃₂O₁₅	488.443
——	O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<>6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1<>6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl acide	80977-05-5	C₃₈H₅₁N₃O₂₅	949.828
——	allyl O-α-D-glucopyranosyl-(1<*>6)-O-α-D-glucopyranoside	136310-62-8	C₁₅H₂₆O₁₁	382.365

反应信息

作为反应物：

描述：

2,3,4,2',3',4',6'-hepta-O-acetyl-α-D-isomaltosyl bromide 在 platinum(IV) oxide 、 Lindlar's catalyst calcium sulfate 、三氯化铝、 sodium azide 、氢气、氰化汞、三乙胺、焦碳酸二乙酯作用下，以四氢呋喃、甲醇、硝基甲烷为溶剂，反应 69.0h，生成 2-amino-4-oxo-4-[[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]amino]butanoic acid

参考文献：

名称：

The nephritogenic glycopeptide from rat glomerular basement membrane. II. Synthesis of O-(.ALPHA.-D-glucopyranosyl)-(1.RAR.6)-O-.BETA.-D-glucopyranosyl-(1.RAR.6)-N-(L-.BETA.-aspartyl)-.ALPHA.-D-glucopyranosylamine (.ALPHA.-D-Glc-(1.RAR.6)-.BETA.-D-Glc-(1.RAR.6)-.ALPHA.-D-Glc-(1.RAR.Asn))

摘要：

O-(α-D-葡萄糖吡喃糖基)-(1→6)-O-β-D-葡萄糖吡喃糖基-(1→6)-N-(L-β-天冬氨酸基)-α-D-葡萄糖胺已经被合成，作为可能存在于大鼠肾小球基底膜中的衍生物模型。这是通过在二乙基磷氰酸酯的存在下，将相应的三糖α-胺与α-乙基苄氧羰基-L-天冬氨酸缩合得到的。随后，通过氢解、去氧乙酰化和去乙氧基化，去除所得到的三糖-氨基酸连接衍生物中的保护基团。对该产物及其相关的糖苷胺衍生物的13C核磁共振谱进行了分析和讨论。

DOI：

10.1248/cpb.29.3196
作为产物：

描述：

β-isomaltose octaacetate 在氢溴酸作用下，以氯仿、溶剂黄146 为溶剂，反应 9.0h，以89.4%的产率得到2,3,4,2',3',4',6'-hepta-O-acetyl-α-D-isomaltosyl bromide

参考文献：

名称：

The nephritogenic glycopeptide from rat glomerular basement membrane. II. Synthesis of O-(.ALPHA.-D-glucopyranosyl)-(1.RAR.6)-O-.BETA.-D-glucopyranosyl-(1.RAR.6)-N-(L-.BETA.-aspartyl)-.ALPHA.-D-glucopyranosylamine (.ALPHA.-D-Glc-(1.RAR.6)-.BETA.-D-Glc-(1.RAR.6)-.ALPHA.-D-Glc-(1.RAR.Asn))

摘要：

O-(α-D-葡萄糖吡喃糖基)-(1→6)-O-β-D-葡萄糖吡喃糖基-(1→6)-N-(L-β-天冬氨酸基)-α-D-葡萄糖胺已经被合成，作为可能存在于大鼠肾小球基底膜中的衍生物模型。这是通过在二乙基磷氰酸酯的存在下，将相应的三糖α-胺与α-乙基苄氧羰基-L-天冬氨酸缩合得到的。随后，通过氢解、去氧乙酰化和去乙氧基化，去除所得到的三糖-氨基酸连接衍生物中的保护基团。对该产物及其相关的糖苷胺衍生物的13C核磁共振谱进行了分析和讨论。

DOI：

10.1248/cpb.29.3196

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文献信息

Synthesis of the α and β anomer of an N-triglycosyl dipeptide

作者：Tadahiro Takeda、Atsushi Utsuno、Naoki Okamoto、Yukio Ogihara、Seiichi Shibata

DOI：10.1016/0008-6215(90)80006-o

日期：1990.10

have been prepared, as models for a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding D-glucosyl-dipeptide derivatives with 2,3,4,2',3',4',6'-hepta-O-acetyl-alpha-D-isomaltopyranosyl bromide in the presence of mercuric cyanide, followed by deprotection of the trisaccharide-dipeptide derivatives.

O-alpha-D-Glucopyranosyl-（1 ---- 6）-O-beta-D-glucopyranosyl-（1 ---- 6）-1-N- [L-aspart-1-oyl-（L-通过将相应的D-葡萄糖基-二肽衍生物与2缩合，制备了脯氨酸）-4-酰基]-α-和-β-D-吡喃葡萄糖基胺，作为大鼠肾小球基底膜中可能存在的衍生物的模型。在氰化汞的存在下，将3,4,2'，3'，4'，6'-庚基-O-乙酰基-α-D-异麦芽吡喃糖基溴化物，然后将三糖-二肽衍生物脱保护。
Characterization of five isomers of branched cyclomaltoheptaose (β CD) having degree of polymerization (d.p.) = 9: Reinvestigation of three positional isomers of diglucosyl-β CD

作者：Kyoko Koizumi、Toshiko Tanimoto (née Utamura)、Yasuyo Okada、Noriko Nakanishi、Nagako Kato、Yosuke Tagaki、Hitoshi Hashimoto

DOI：10.1016/0008-6215(91)84013-5

日期：1991.8

has been newly isolated from a glucosyl-beta CD mixture prepared by hydrolysis with glucoamylase of a maltosyl-beta CD mixture, synthesized from maltose and beta CD through the reverse action of pullulanase. Chromatographic behavior and spectral data (13C-n.m.r. and f.a.b.-m.s.) of these isomers of branched beta CD (1-4), as well as those of another isomer prepared by the reverse action of hydrolytic

通过甲基化分析和化学合成已证实，从带有大芽孢杆菌环麦芽糖糊精葡聚糖转移酶的大规模制备β-CD的母液中分离出的支链环麦芽七糖（βCD）的三个异构体是6（1），6（4）-二-O-（α-D-吡喃葡萄糖基）-环麦芽庚糖（1），6（1），6（3）-二-O-（α-D-吡喃葡萄糖基）-环麦芽庚糖（2）和6-O- α-异麦芽糖基）-环麦芽庚糖（4）代替了6（1），6（2）-二-O-（α-D-吡喃葡萄糖基）-麦芽七糖（3），这在先前的论文中被错误地描述了。已经从通过用葡糖淀粉酶的逆作用由麦芽糖和βCD合成的麦芽糖β-CD混合物的葡糖淀粉酶水解制备的葡糖基-βCD混合物中新分离了化合物3。色谱行为和光谱数据（13C-nmr和fa
The Nephritogenic Glycopeptide from Rat Glomerular Basement Membrane. X. Synthesis of an N-Triglycosyl Dipeptide and Characteristics of Its cis-trans Isomers.

作者：Tadahiro TAKEDA、Keisuke KOJIMA、Yukio OGIHARA

DOI：10.1248/cpb.39.2699

日期：——

Isomers of O-α-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→6)-N-[L-aspart-1-onl-(L-proline)4-oyl]-α-D-glucopyranosylamine have been prepared, as models for a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding dipeptide derivative (5) with triglycosylamine (4) in the presence of O, O-diethylcyanophosphonate, followed by deprotection of the trisaccharide-dipeptide derivative. During the deprotection process, cis- and trans-isomers containing proline were separated by silica gel column chromatography and also reversed-phase high performance liquid chromatography.

通过在O, O-二乙基氰基磷酸酯存在下，将相应的二肽衍生物（5）与三糖胺（4）缩合，然后对三糖-二肽衍生物进行脱保护，制备了O-α-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基-(1→6)-N-[L-天冬氨酰-1-酮-(L-脯氨酸)4-酰基]-α-D-吡喃葡萄糖胺的异构体，作为可能存在于大鼠肾小球基底膜中的衍生物的模型。在脱保护过程中，通过硅胶柱色谱法以及反相高效液相色谱法分离出含有脯氨酸的顺式和反式异构体。
Electrochemical Glycosylation via Halogen-Atom-Transfer for C-Glycoside Assembly

作者：Jun Wu、Rajeshwaran Purushothaman、Felix Kallert、Simon L. Homölle、Lutz Ackermann

DOI：10.1021/acscatal.4c02322

日期：2024.8.2

Glycosyl donor activation emerged as an enabling technology for anomeric functionalization, but aimed primarily at O-glycosylation. In contrast, we herein disclose mechanistically distinct electrochemical glycosyl bromide donor activations via halogen-atom transfer and anomeric C-glycosylation. The anomeric radical addition to alkenes led to C-alkyl glycoside synthesis under precious metal-free reaction

糖基供体激活是作为异头功能化的一项可行技术而出现的，但主要针对O-糖基化。相反，我们在此公开了通过卤素原子转移和异头C-糖基化的机械上不同的电化学糖基溴供体激活。异头自由基加成到烯烃上导致在无贵金属的反应条件下从容易获得的糖基溴合成C1-烷基糖苷。我们的 e-XAT 策略的稳健性通过镍电催化的C-芳基和C-酰基糖苷组装得到了进一步体现。我们的方法为糖基供体激活提供了一种正交策略，具有方便的范围，因此代表了直接C-糖苷组装的通用方法。
Synthesis of poly-O-sulfated glycosides of 2,5-anhydro-d-mannitol

作者：János Kuszmann、Gábor Medgyes、Sándor Boros

DOI：10.1016/j.carres.2005.05.006

日期：2005.7

2,5-Anhydro-3-O-beta-D-glucopyranosyl-; -3-O-alpha-D-idopyranosyl-; -3-O-alpha-D-arabinopyranosyl-; -3-O-alpha-L-arabinopyranosyl--; -3-0-beta-D-maltopyranosyl-; -3-O-beta-D-gentiobiopyranosyl-; -1,6-di-O-beta-D-glucopyranosyl-; -1,6-di-O-alpha-L-idopyranosyl,-; -1-O-beta-D-maltopyranosyl-.- -1,3,.6-tri-O-beta-D-glucopyranosyl-; -1,6-di-O-beta-maltopyranosyl- and -1,6-di-O-beta-D-gentiobiopyranosyl-2,5-anhydro-D-mannitol as well as their poly-O-sulfated derivatives were synthesized. The IP3-IC50 values of their sodium and/or potassium salts were determined for structure-activity studies aiming at the synthesis of new, orally active antiasthmatic compounds. (c) 2005 Elsevier Ltd. All rights reserved.