1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside | 56822-49-2

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

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

英文别名

(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate；1-O-acetyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside；1-O-acetyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose；acetyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] acetate

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside化学式

CAS

56822-49-2

化学式

C₃₆H₃₈O₇

mdl

——

分子量

582.694

InChiKey

YYFLBSFJOGQSRA-GJXDWMKPSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

677.2±55.0 °C(Predicted)
密度：

1.21±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

5.6
重原子数：

43
可旋转键数：

15
环数：

5.0
sp3杂化的碳原子比例：

0.31
拓扑面积：

72.4
氢给体数：

0
氢受体数：

7

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-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose	80300-30-7	C₃₆H₃₈O₇	582.694
甲基 2,3,4,6-O-四苄基-alpha-D-吡喃葡萄糖苷	methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside	17791-37-6	C₃₅H₃₈O₆	554.683
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
2,3,4,6-四-o-苄基-D-吡喃葡萄糖	2,3,4,6-tetra-O-benzyl-D-glucopyranose	6564-72-3	C₃₄H₃₆O₆	540.656
——	2,3,4,6-tetra-O-benzyl-D-glucopyranoside	59531-24-7	C₃₄H₃₆O₆	540.656
——	1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside	30608-21-0	C₃₇H₄₄O₆Si	612.838
——	2,3,4,6-tetra-O-benzyl-1-O-(N-4-methylphenyl)diphenylacetimidyl-β-D-glucopyranose	74808-05-2	C₅₅H₅₃NO₆	824.029
甲基-Alpha-D-吡喃葡糖苷	methyl D-glucopyranoside	3149-68-6	C₇H₁₄O₆	194.185
2,3,4,6-四-O-苄基-D-吡喃葡萄糖酰氟	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride	122741-44-0	C₃₄H₃₅FO₅	542.647

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside	78890-53-6	C₃₆H₄₀O₆	568.71
——	methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside	——	C₆₂H₆₆O₁₁	987.199
——	methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside	——	C₆₂H₆₆O₁₁	987.199
——	methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside	77117-44-3	C₆₂H₆₆O₁₁	987.199
——	methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside	64694-18-4	C₆₂H₆₆O₁₁	987.199
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-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate	124813-78-1	C₃₇H₄₀O₇	596.72
——	methyl 2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)acetate	114192-64-2	C₃₇H₄₀O₇	596.72
——	1-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-2-propanon	85422-90-8	C₃₇H₄₀O₆	580.721
——	(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)ethyne	139195-28-1	C₃₆H₃₆O₅	548.679
——	α-1,5-anhydro-1-C-(2-trimethylsilylethynyl)-2,3,4,6-tetra-O-benzyl-D-glucitol	141100-79-0	C₃₉H₄₄O₅Si	620.861
——	2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl iodide	53008-62-1	C₃₄H₃₅IO₅	650.553
2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖酰氟	2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride	78153-79-4	C₃₄H₃₅FO₅	542.647
2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖酰氟	2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride	89025-46-7	C₃₄H₃₅FO₅	542.647
——	(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)phenylacetylene	113794-27-7	C₄₂H₄₀O₅	624.777

反应信息

作为反应物：

描述：

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 在 10percent Pd/C 三氟化硼乙醚、氢气作用下，以甲醇、二氯甲烷、乙腈为溶剂， 20.0 ℃ 、101.33 kPa 条件下，反应 26.0h，生成 (3R,5S)-3-((R)-13-Hydroxy-13-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-5-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-tridecyl)-5-methyl-dihydro-furan-2-one

参考文献：

名称：

Synthesis, Spectroscopy, and Cytotoxicity of Glycosylated Acetogenin Derivatives as Promising Molecules for Cancer Therapy

摘要：

Several glycosyl derivatives of squamocin (1) have been synthesized by glycosylation under Lewis acid catalysis with two different 1-O-acetyl sugars. Separation of these compounds has been achieved by HPLC and centrifugal partition chromatography (CPC). A detailed NMR, ESIMS, and LSIMS study allowed complete structural elucidations. The cytotoxic activity of the glycosyl derivatives was investigated and compared with that of squamocin and drosquamocin against human epidermoid carcinoma cells (KB), African green monkey (Cercopithecus aethiops) kidney epithelial cells (VERO), and mouse lymphocytic leukemia cells (L1210). The antiproliferative effects of some derivatives were studied on cell cycles in mouse lymphocytic leukemia cells (L1210).