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1-phenylsulfenyl-3,4,6-tri-O-acetyl-1,2-dideoxy-2-N-tetrachlorophthalimido-β-D-glucopyranoside | 217814-68-1

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

1-phenylsulfenyl-3,4,6-tri-O-acetyl-1,2-dideoxy-2-N-tetrachlorophthalimido-β-D-glucopyranoside

英文别名

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-tetrachlorophthalimido-1-thio-β-D-glucopyranoside；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate

1-phenylsulfenyl-3,4,6-tri-O-acetyl-1,2-dideoxy-2-N-tetrachlorophthalimido-β-D-glucopyranoside化学式

CAS

217814-68-1

化学式

C₂₆H₂₁Cl₄NO₉S

mdl

——

分子量

665.332

InChiKey

ABPNGSRRWRSTHR-GTXXOPQDSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

741.4±60.0 °C(Predicted)
密度：

1.60±0.1 g/cm3(Predicted)
溶解度：

可溶于乙酸乙酯，DCM

计算性质

辛醇/水分配系数(LogP)：

5.3
重原子数：

41
可旋转键数：

10
环数：

4.0
sp3杂化的碳原子比例：

0.35
拓扑面积：

151
氢给体数：

0
氢受体数：

10

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
——	1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-α-D-glucopyranoside	183388-13-8	C₂₂H₁₉Cl₄NO₁₁	615.205
2-脱氧-2-(四氯苯二甲酰亚胺基)-D-吡喃葡萄糖-1,3,4,6-四乙酸盐	1,3,4,5-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-D-glucopyranose	174356-26-4	C₂₂H₁₉Cl₄NO₁₁	615.205

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	[(2R,3S,4R,5R,6S)-3-hydroxy-2-(phenylmethoxymethyl)-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-4-yl] acetate	874364-55-3	C₂₉H₂₃Cl₄NO₇S	671.382
——	phenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-(3,4,5,6-tetrachlorophthalimido)-β-D-thioglucopyranoside	404391-07-7	C₂₉H₂₁Cl₄NO₇S	669.366
——	[(2R,3S,4R,5R,6S)-4-benzoyloxy-2-(hydroxymethyl)-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-3-yl] benzoate	874364-56-4	C₃₄H₂₃Cl₄NO₈S	747.437
——	phenyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside	286018-83-5	C₂₀H₁₅Cl₄NO₆S	539.22
——	Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-4-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester	217814-71-6	C₄₁H₃₉Cl₄NO₁₅S	959.636
——	Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester	217814-73-8	C₄₄H₄₁Cl₄NO₁₂S	949.687
——	phenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside	217814-69-2	C₂₇H₂₁Cl₄NO₆S	629.345
——	Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-4-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester	217814-74-9	C₄₄H₄₁Cl₄NO₁₂S	949.687
——	4,5,6,7-Tetrachloro-2-((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione	404391-02-2	C₂₇H₁₉Cl₄NO₆S	627.329
——	(2R,3S,4R,5R,6S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-(phenylthio)-5-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)tetrahydro-2H-pyran-3,4-diyl dibenzoate	922182-98-7	C₄₀H₃₇Cl₄NO₈SSi	861.699
——	3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranose	215314-53-7	C₂₀H₁₇Cl₄NO₁₀	573.168
——	Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester	217814-70-5	C₂₈H₃₅Cl₄NO₁₀Si	715.484
——	O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-[(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl trichloroacetimidate	217814-79-4	C₅₄H₅₅Cl₇N₂O₂₂	1332.2
——	thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside	217814-90-9	C₆₀H₇₃Cl₄NO₂₂Si	1330.13
——	thexyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-[(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside	217814-87-4	C₆₀H₇₃Cl₄NO₂₂Si	1330.13
——	[(2S,3R,4R,5S,6S)-4-acetyloxy-6-[(2S,3R,4R,5S,6R)-2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-5-hydroxy-6-(phenylmethoxymethyl)-3-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-4-yl]oxy-2-methyl-5-phenylmethoxyoxan-3-yl] acetate	217814-88-5	C₄₆H₅₅Cl₄NO₁₃Si	999.839
——	[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-4-hydroxy-2-(phenylmethoxymethyl)-5-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-3-yl]oxyoxan-2-yl]methyl acetate	217814-86-3	C₄₃H₅₃Cl₄NO₁₆Si	1009.79

反应信息

作为反应物：

描述：

1-phenylsulfenyl-3,4,6-tri-O-acetyl-1,2-dideoxy-2-N-tetrachlorophthalimido-β-D-glucopyranoside 在咪唑、 N-溴代丁二酰亚胺(NBS) 、三氟甲磺酸三甲基硅酯、 sodium methylate 、四丁基碘化铵、三乙胺、三丁基氧化锡作用下，以甲醇、二氯甲烷、水、 N,N-二甲基甲酰胺、丙酮为溶剂，反应 38.42h，生成 thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

参考文献：

名称：

Lay, Luigi; Manzoni, Leonardo; Schmidt, Richard R., Carbohydrate Research, 1998, vol. 310, # 3, p. 159 - 172

摘要：

DOI：
作为产物：

描述：

苯硫酚、 2-脱氧-2-(四氯苯二甲酰亚胺基)-D-吡喃葡萄糖-1,3,4,6-四乙酸盐在三氯化铁作用下，以二氯甲烷为溶剂，反应 1.0h，以91%的产率得到1-phenylsulfenyl-3,4,6-tri-O-acetyl-1,2-dideoxy-2-N-tetrachlorophthalimido-β-D-glucopyranoside

参考文献：

名称：

Lay, Luigi; Manzoni, Leonardo; Schmidt, Richard R., Carbohydrate Research, 1998, vol. 310, # 3, p. 159 - 172

摘要：

DOI：

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文献信息

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DOI：10.1002/anie.200602699

日期：2006.11.20
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DOI：10.1016/j.carres.2011.03.033

日期：2011.7

1,2-cis-Glycosyl acetates with the alpha-configuration were revealed to be very unreactive towards Lewis acid catalyzed thioglycosylations. Optimal and cost-effective conditions for enabling this direct conversion is absent in the literature. Our studies have shown that elevating the reaction temperature with a catalytic amount of BF3 center dot OEt2 was more effective than changing Lewis acids with higher acidities to accommodate the low reactivity of alpha-glycosyl acetates. The effect of impurities in stored BF3 center dot OEt2 on the reaction is also discussed. (C) 2011 Elsevier Ltd. All rights reserved.
Highly Diastereoselective Oxidation of 2-Amino-2-deoxy-1-thio-β-<scp>d</scp>-glucopyranosides: Synthesis of Imino Sulfinylglycosides

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A synthetic route to imino thioglycosides and to imino sulfinylglycosides has been developed. A detailed study on the diastereoselective oxidation of 2-amino-2-deoxy-1-thio-beta-D-glucopyranosides is reported. It has been shown that the stereochemical outcome of the oxidation is highly dependent on the protective group of the amine function. While the oxidation of iminothioglycosides is slightly diastereoselective (up to 30% de in favor of the R-S sulfoxide), a single isomer is obtained in the case of tetrachloroplithalimido derivatives. The absolute configuration of the sulfinyl glycoside was ascertained by NMR analysis using our recent model on the basis of the exo-anomeric effect corroborated by X-ray crystallography.
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