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苄基 2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧-alpha-D-吡喃葡萄糖苷 | 82827-77-8

分子结构分类

有机化合物 - 有机氧化合物

中文名称

苄基 2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧-alpha-D-吡喃葡萄糖苷

中文别名

3-氰基-2-氟苯甲酸；苄基2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧-alpha-D-吡喃葡萄糖苷；苄基2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧-Α-D-吡喃葡糖苷

英文名称

Benzyl-2-acetamido-2-desoxy-3,6-di-O-dibenzoyl-α-D-glucopyranosid

英文别名

Benzyl-2-acetamido-3,6-di-O-benzoyl-2-desoxy-α-D-glucopyranosid；benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside；2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside；Benzyl 2-Acetamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside；[(2R,3S,4R,5R,6S)-5-acetamido-4-benzoyloxy-3-hydroxy-6-phenylmethoxyoxan-2-yl]methyl benzoate

苄基 2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧-alpha-D-吡喃葡萄糖苷化学式

CAS

82827-77-8

化学式

C₂₉H₂₉NO₈

mdl

——

分子量

519.551

InChiKey

MYVKGGKJMHXHHZ-FSJVOCHISA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

159-160°C

计算性质

辛醇/水分配系数(LogP)：

3.4
重原子数：

38
可旋转键数：

11
环数：

4.0
sp3杂化的碳原子比例：

0.28
拓扑面积：

120
氢给体数：

2
氢受体数：

8

SDS

SDS：ef217c1b382d83c49201d7f3197ec089

查看

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
——	benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside	33423-31-3	C₂₂H₂₅NO₇	415.443
苄基-2-乙酰胺基-2-脱氧-Alpha-D-吡喃葡萄糖苷	benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside	13343-62-9	C₁₅H₂₁NO₆	311.335

下游产品

中文名称	英文名称	CAS号	化学式	分子量
苄基2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧吡喃己糖苷	Benzyl-2-acetamido-3,6-di-O-benzoyl-2-desoxy-α-D-galactopyranosid	141019-70-7	C₂₉H₂₉NO₈	519.551
——	benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-α-D-glucopyranoside	174866-50-3	C₆₃H₅₅NO₁₇	1098.13
苄基-2-乙酰胺基-2-脱氧-Alpha-D-吡喃半乳糖苷	benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside	3554-93-6	C₁₅H₂₁NO₆	311.335
——	benzyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside	290819-68-0	C₂₉H₂₈FNO₇	521.542
——	N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]acetamide	174866-45-6	C₂₁H₃₁NO₁₁	473.477
苄基 2-乙酰氨基-3,6-二-O-苯甲酰基-2,4-二脱氧-4-氟-alpha-D-吡喃葡萄糖苷	benzyl 2-acetamido-2,4-dideoxy-4-fluoro-β-D-glucopyranoside	290819-73-7	C₁₅H₂₀FNO₅	313.326
——	2-(Acetylamino)-2-Deoxy-4-O-Beta-D-Galactofuranosyl-Alpha-D-Glucopyranose	174866-48-9	C₁₄H₂₅NO₁₁	383.353
2-乙酰氨基-2,4-二脱氧-4-氟-d-吡喃葡萄糖	2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose	116049-57-1	C₁₄H₂₀FNO₈	349.313
——	2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranose	——	C₈H₁₅NO₅	205.211

反应信息

作为反应物：

描述：

苄基 2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧-alpha-D-吡喃葡萄糖苷在 palladium on activated charcoal 吡啶、氢氧化钾、二乙胺基三氟化硫、氢气、 sodium nitrite 作用下，以甲醇、二氯甲烷、溶剂黄146 、 N,N-二甲基甲酰胺为溶剂， -5.0~20.0 ℃ 、379.21 kPa 条件下，反应 88.83h，生成 2-acetamido-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose

参考文献：

名称：

Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-galactose and their effects on cellular glycosaminoglycan biosynthesis

摘要：

4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-gala (31) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation to 1 and 9%. respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [C-14]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0008-6215(00)00049-5
作为产物：

描述：

苯甲酰氯、 benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 在吡啶作用下，反应 10.0h，以88%的产率得到苄基 2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧-alpha-D-吡喃葡萄糖苷

参考文献：

名称：

Synthesis of 4-acetamido-N-acetyl-4-deoxy- and 4,6-di(acetamido)-N-acetyl-4,6-dideoxy-muramoyl-l-alanyl-d-isoglutamine derivatives

摘要：

DOI：

10.1016/s0008-6215(00)80689-8

点击查看最新优质反应信息

文献信息

3- and 4-Uloses Derived from N-Acetyl-D-glucosamine: A Unique Pair of Complementary Organocatalysts for Asymmetric Epoxidation of Alkenes

作者：Christof Schöberl、Volker Jäger

DOI：10.1002/adsc.201100735

日期：2012.3.16

The 4‐ulose and the 3‐ulose, both derived in two steps from the α‐methyl glycoside of N‐acetyl‐D‐glucosamine (GlcNAc), act as organocatalysts in the asymmetric epoxidation of alkenes, with unprecedented complementary enantioselectivity. The best results are found with α,β‐unsaturated esters as substrates, with enantiomeric ratios up to 90:10 and 11:89, respectively.

N-乙酰基-D-葡糖胺（GlcNAc）的α-甲基糖苷（GlcNAc）分两步衍生出来的4-ulose和3-ulose在烯烃的不对称环氧化中起有机催化剂的作用，具有前所未有的互补对映选择性。以α，β-不饱和酯为底物发现最佳结果，对映体比例分别高达90:10和11:89。
Hydrogenphosphonate synthesis of sugar phosphomonoesters

作者：Dmitry V. Yashunsky、Andrei V. Nikolaev

DOI：10.1039/b000727g

日期：——

A highly efficient procedure for the phosphorylation of sugar hydroxy derivatives has been developed. A four-step sequence comprising H-phosphonate formation, pivaloyl chloride-mediated coupling with fluoren-9-ylmethanol, oxidation, and cleavage of the fluoren-9-ylmethyl ester led to the sugar monophosphate derivatives 4a–g in 83–93% yield.

已经开发了一种高效的糖羟基衍生物磷酸化程序。该程序包括四个步骤：H-磷酸酯的形成、与弗罗伦-9-甲醇的pivaloyl氯介导的耦合、氧化以及弗罗伦-9-甲基酯的裂解，最终获得糖单磷酸衍生物4a-g，产率为83-93%。
Kamiya, Shintaro; Esaki, Sachiko; Shiba, Naoko, Agricultural and Biological Chemistry, 1987, vol. 51, # 4, p. 1195 - 1198

作者：Kamiya, Shintaro、Esaki, Sachiko、Shiba, Naoko

DOI：——

日期：——
Paulsen, Hans; Rutz, Volker; Brockhausen, Inka, Liebigs Annalen der Chemie, 1992, # 7, p. 735 - 746

作者：Paulsen, Hans、Rutz, Volker、Brockhausen, Inka

DOI：——

日期：——
Synthesis of 4-deoxy analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-xylose and their effects on glycoconjugate biosynthesis

作者：Ali Berkin、Mark A Szarek、Jan Plenkiewicz、Walter A Szarek*、Robert Kisilevsky*

DOI：10.1016/s0008-6215(99)00314-6

日期：2000.3

4-Deoxy analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-xylose were synthesized and evaluated as inhibitors of glycoconjugate biosynthesis. Methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside (11) showed a reduction in [H-3]GlcN and [C-14]Leu incorporation into hepatocyte cellular glycoconjugates by 89 and 88%, of the control cells, respectively, at 20 mM, whereas the free sugars, 2-acetamido-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses (15), showed a reduction of [H-3]GlcN and [C-14]Leu incorporation by 75 and 64%, respectively, at 20 mM. The acetylated analogues of 11 and 15, namely methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-beta-D-xylo-hexopyranoside and 2-acetamido-1.3,6-tri-O-acetyl-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses, showed a greater inhibition of [H-3]GlcN and [C-14]Leu incorporation at 1 mM compared with their non-acetylated counterparts, but were toxic to hepatocytes at concentrations of 10 and 20 mM. Corresponding derivatives of 2-acetamido-2,4-dideoxy-L-threo-pentopyranose showed no biological effect up to 20 mM, suggesting that the C-6 substituent is important for the biological activity. (C) 2000 Elsevier Science Ltd. All rights reserved.