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Methyl-5-(acetylamino)-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester | 105252-44-6

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-5-(acetylamino)-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester

英文别名

methyl (methyl 5-acetamido-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-β-D-galacto-non-2-ulopyranosid)onate；methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2-methoxyoxane-2-carboxylate

Methyl-5-(acetylamino)-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester化学式

CAS

105252-44-6

化学式

C₂₂H₄₁NO₉Si

mdl

——

分子量

491.654

InChiKey

GYZDPVWEIVGPTK-YPJKBPGMSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

571.6±50.0 °C(Predicted)
密度：

1.15±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

1.7
重原子数：

33
可旋转键数：

9
环数：

2.0
sp3杂化的碳原子比例：

0.91
拓扑面积：

122
氢给体数：

2
氢受体数：

9

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
5-乙酰氨基-3,5-二脱氧-6-(1,2,3-三羟基丙基)己-2-酮吡喃糖苷酸二甲基酯	N-Acetyl-β-D-neuraminylsaeure-methyl-methylglycosid	6730-43-4	C₁₃H₂₃NO₉	337.327

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-propoxymethyl]-2-methoxyoxane-2-carboxylate	474801-28-0	C₂₅H₄₇NO₉Si	533.735
——	(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-dodecyloxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	474801-36-0	C₃₄H₆₅NO₉Si	659.977
——	(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentyloxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	474801-30-4	C₂₇H₅₁NO₉Si	561.789
——	(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-octyloxy-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	474801-33-7	C₃₀H₅₇NO₉Si	603.869
——	(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-[2-(2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	548759-51-9	C₃₁H₅₇NO₁₁Si	647.879
——	methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-pent-4-enoxymethyl]-2-methoxyoxane-2-carboxylate	374603-95-9	C₂₇H₄₉NO₉Si	559.773
——	(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-(2,2-difluoro-but-3-enyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	374604-56-5	C₂₆H₄₅F₂NO₉Si	581.727
——	(2S,4S,5R,6R)-5-Acetylamino-6-[(S)-allyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-4-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	548759-70-2	C₁₉H₃₁NO₉	417.456
——	(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((2R,3R,4R)-3,4-dihydroxy-tetrahydro-furan-2-yl)-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	548759-63-3	C₁₆H₂₅NO₁₀	391.375
——	(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1-allyloxy-2,3-dihydroxy-propyl)-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	374603-53-9	C₁₈H₂₉NO₁₀	419.429
——	(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxy-6-((R)-1-pent-4-enyloxy-allyl)-tetrahydro-pyran-2-carboxylic acid methyl ester	548759-60-0	C₂₀H₃₁NO₈	413.468
——	(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((R)-1-allyloxy-allyl)-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	548759-59-7	C₁₈H₂₇NO₈	385.414
——	(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-(R)-2,5-dihydro-furan-2-yl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester	548759-61-1	C₁₆H₂₃NO₈	357.361
——	(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxy-6-(R)-2,5,6,7-tetrahydro-oxepin-2-yl-tetrahydro-pyran-2-carboxylic acid methyl ester	548759-62-2	C₁₈H₂₇NO₈	385.414
——	(4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((2S,3R,4R)-3,4-diacetoxy-tetrahydro-furan-2-yl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	548759-77-9	C₁₉H₂₅NO₁₁	443.408
——	(4S,5R,6R,1'S,2'R)-5-acetylamino-4-(bis-N,N'-tert-butyloxycarbonyl)-guanidino-6-(2',3'-diacetoxy-1'-tetradecyloxy)propyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	474801-72-4	C₄₁H₇₀N₄O₁₃	827.026
——	(4S,5R,6R)-5-Acetylamino-6-((2R,3R,4R)-3,4-dihydroxy-tetrahydro-furan-2-yl)-4-guanidino-5,6-dihydro-4H-pyran-2-carboxylic acid	——	C₁₃H₂₀N₄O₇	344.324

反应信息

作为反应物：

描述：

Methyl-5-(acetylamino)-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester 在 Lindlar's catalyst 吡啶、 4-二甲氨基吡啶、四氧化锇、 Grubbs catalyst first generation 、 sodium azide 、 Dowex 50W (H⁺) 、硫酸、四丁基氟化铵、氢气、 sodium hydride 、溶剂黄146 、 N-甲基吗啉氧化物、三甲氧基磷作用下，以四氢呋喃、乙醇、二氯甲烷、 N,N-二甲基甲酰胺、丙酮、叔丁醇为溶剂，生成 (4R,5R,6R)-5-Acetylamino-4-amino-6-((2S,3R,4R)-3,4-diacetoxy-tetrahydro-furan-2-yl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

参考文献：

名称：

Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

摘要：

We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0960-894x(02)01039-9
作为产物：

描述：

5-乙酰氨基-3,5-二脱氧-6-(1,2,3-三羟基丙基)己-2-酮吡喃糖苷酸二甲基酯在咪唑、对甲苯磺酸作用下，以二氯甲烷为溶剂，反应 2.0h，生成 Methyl-5-(acetylamino)-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester

参考文献：

名称：

N-乙酰神经氨酸的氧化脱氨：取代基效应和机制

摘要：

研究 N-亚硝基-N-乙酰基唾液酸糖苷的氧化脱氨机制，从而整体保留相应的 2-酮-3-脱氧-D-甘油-D-半乳糖-壬基吡喃糖苷酸 (KDN)利用一系列差异性 O-保护的 N-亚硝基-N-乙酰基唾液酸糖苷和同位素标记研究描述了糖苷。没有发现 4- 和 7- 位酯基参与立体定向的证据。比较了 4-氨基-4-脱氧和 2-氨基-2-脱氧吡喃己糖苷的氧化脱氨反应，并制定了一个共同机制，涉及吡喃糖苷参与后 1-氧杂双环[3.1.0]己基氧鎓离子的中介作用环氧。通过对 β-硫唾液酸苷的标记研究发现了一条次要反应途径，该途径导致 4-O-乙酰基被冰醋酸交换，冰醋酸在一般氧化脱氨过程中充当外部亲核试剂。提出了一种涉及硫代糖苷在中间体重氮烷水平参与的交换机制。

DOI：

10.1021/jacs.5b13015

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文献信息

Synthesis and anti-Influenza virus activity of 7-O-Alkylated derivatives related to zanamivir

作者：Takeshi Honda、Takeshi Masuda、Shuku Yoshida、Masami Arai、Satoru Kaneko、Makoto Yamashita

DOI：10.1016/s0960-894x(02)00329-3

日期：2002.8

A series of 7-alkyl ether derivatives related to zanamivir were synthesized using direct alkylation of the C-7 alcohol of sialic acid. Alkyl ether moiety of less than 12 carbons in length showed low nanomolar inhibitory activity against influenza A virus sialidase. Furthermore, their moiety improved influenza A virus plaque reduction activity compared to zanamivir. However, removal of the 8,9-diol of the 7-O-alkyl derivatives resulted in loss of antiviral potency. This result suggests that 8,9-diol must play an important role in binding with both influenza A and B virus sialidases. (C) 2002 Elsevier Science Ltd. All rights reserved.
Strukturelle Abwandlungen an N-Acetylneuramins�uren, 8 Synthese von 7-, 8-, 9-Desoxy- und 4,7-Didesoxyneuramins�ure

作者：Erich Zbiral、Hannelore H. Brandstetter、Erwin P. Schreiner

DOI：10.1007/bf00810094

日期：1988.1
Bioorg. Med. Chem. Lett. 2002, 12, 1925-1928

作者：

DOI：——

日期：——
ZBIRAL, ERICH;BRANDSTETTER, HANNELORE H.;SCHREINER, ERWIN P., MONATSH. CHEM., 119,(1988) N 1, 127-141

作者：ZBIRAL, ERICH、BRANDSTETTER, HANNELORE H.、SCHREINER, ERWIN P.

DOI：——

日期：——
Zbiral, Erich; Phadtare, Shashikant; Schmid, Walther, Liebigs Annalen der Chemie, 1987, p. 39 - 44

作者：Zbiral, Erich、Phadtare, Shashikant、Schmid, Walther

DOI：——

日期：——