O-(2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate | 120449-23-2

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

O-(2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate

英文别名

2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl trichloroacetimidate；(2R,3R,4S,5R,6R)-2-Methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate

O-(2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate化学式

CAS

120449-23-2

化学式

C₁₄H₁₈Cl₃NO₈

mdl

——

分子量

434.658

InChiKey

CBEDSVQSHODOKN-NOWHUZAPSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

404.0±55.0 °C(Predicted)
密度：

1.55±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.2
重原子数：

26
可旋转键数：

8
环数：

1.0
sp3杂化的碳原子比例：

0.71
拓扑面积：

121
氢给体数：

1
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
——	1,2,3,4-tetra-O-acetyl-6-deoxy-α-D-glucopyranose	7404-35-5	C₁₄H₂₀O₉	332.307

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	Acetic acid (2S,3R,4S,5R,6R)-3,5-diacetoxy-2-((R)-1,5-dimethyl-1-vinyl-hex-4-enyloxy)-6-methyl-tetrahydro-pyran-4-yl ester	791080-18-7	C₂₂H₃₄O₈	426.507
——	[(2R,3R,4S,5R,6S)-6-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]oxy-2-methyl-4,5-bis(4-oxopentanoyloxy)oxan-3-yl] (2E,6R)-2,6-dimethyl-6-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyocta-2,7-dienoate	791080-46-1	C₅₀H₇₂O₂₀	993.11
——	[(2R,3R,4S,5R,6S)-2-methyl-6-[(3R)-3-methyl-6-oxohex-1-en-3-yl]oxy-4,5-bis(4-oxopentanoyloxy)oxan-3-yl] (2E,6R)-2,6-dimethyl-6-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyocta-2,7-dienoate	791080-54-1	C₄₇H₆₆O₂₁	967.028
——	4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-((R)-1,5-dimethyl-1-vinyl-hex-4-enyloxy)-3,5-dihydroxy-6-methyl-tetrahydro-pyran-4-yl ester	791080-36-9	C₂₁H₃₄O₇	398.497
——	4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-5-[2-(diethoxy-phosphoryl)-propionyloxy]-2-((R)-1,5-dimethyl-1-vinyl-hex-4-enyloxy)-6-methyl-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-3-yl ester	791080-42-7	C₃₃H₅₃O₁₃P	688.75
——	4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3-[2-(diethoxy-phosphoryl)-propionyloxy]-6-((R)-1,5-dimethyl-1-vinyl-hex-4-enyloxy)-5-hydroxy-2-methyl-tetrahydro-pyran-4-yl ester	791080-60-9	C₂₈H₄₇O₁₁P	590.648
——	3β-tert-butyldimethylsilyloxy-6α-(2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranosyloxy)-5α-pregn-9(11)-en-20-one	155223-86-2	C₃₉H₆₂O₁₀Si	719.001

反应信息

作为反应物：

描述：

O-(2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate 在 palladium dihydroxide sodium hydroxide 、 4 A molecular sieve 、 Dowex 1 * 8-200 (Cl^- form) 、氢气、 potassium carbonate 、三甲基膦作用下，以四氢呋喃、甲醇、二氯甲烷、水、溶剂黄146 为溶剂，反应 27.0h，生成 TC020

参考文献：

名称：

Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability: The SAR of d-Pyranoses on Ring III of Pyranmycin

摘要：

The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.

DOI：

10.1021/ol0269042
作为产物：

描述：

2,3,4-Tri-O-acetyl-6-deoxy-D-glucopyranose 生成 O-(2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate

参考文献：

名称：

LIU, LI-DA;LIU, HUNG-WEN, TETRAHEDRON LETT., 30,(1989) N 1, C. 35-36

摘要：

DOI：

点击查看最新优质反应信息

文献信息

Chloromethyl Glycosides as Versatile Synthons to Prepare Glycosyloxymethyl‐Prodrugs

作者：Hidde Elferink、Willem H. C. Titulaer、Maik G. N. Derks、Gerrit H. Veeneman、Floris P. J. T. Rutjes、Thomas J. Boltje

DOI：10.1002/chem.202103910

日期：2022.2.16

Monosaccharides were introduced on drug molecules to improve their solubility, metabolic stability and oral bioavailability. A new chloromethyl glycoside synthon was developed to enable the synthesis of numerous monosaccharide prodrugs.

在药物分子上引入单糖以提高其溶解度、代谢稳定性和口服生物利用度。开发了一种新的氯甲基糖苷合成子，能够合成多种单糖前药。
Synthesis of Dimeric Terpenoyl Glycoside Side Chains from Cytotoxic Saponins

作者：Sabine Reicheneder、Carlo Unverzagt

DOI：10.1002/anie.200352895

日期：2004.8.20
Jiang, Zi-Hua; Han, Xiao-Bing; Schmidt, Richard R., Liebigs Annalen der Chemie, 1993, # 11, p. 1179 - 1184

作者：Jiang, Zi-Hua、Han, Xiao-Bing、Schmidt, Richard R.

DOI：——

日期：——
Jiang, Zi-Hua; Schmidt, Richard R., Liebigs Annalen der Chemie, 1992, # 9, p. 975 - 982

作者：Jiang, Zi-Hua、Schmidt, Richard R.

DOI：——

日期：——
NEW CATECHOLAMINE PRODRUGS FOR USE IN THE TREATMENT OF PARKINSON'S DISEASE

申请人：H. Lundbeck A/S

公开号：US20220213071A1

公开（公告）日：2022-07-07

The present invention provides compounds of formula (Id) that are prodrugs of catecholamine for use in treatment of neurodegenerative diseases and disorders. The present invention also provides pharmaceutical compositions comprising compounds of the invention and methods of treating neurodegenerative or neuropsychiatric diseases and disorders using the compounds of the invention, in particular Parkinson's disease.