methyl (2S,3S,4S,5R,6R)-3-[[(4aR,6S,7R,8R,8aS)-8-[(2R,3R,4S,5S,6S)-5-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-(4-oxopentanoyloxy)-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-3,4-dibenzoyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate | 1158797-06-8

分子结构分类

有机化合物 - 脂质和类脂质分子 - 糖脂

中文名称

——

中文别名

——

英文名称

methyl (2S,3S,4S,5R,6R)-3-[[(4aR,6S,7R,8R,8aS)-8-[(2R,3R,4S,5S,6S)-5-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-(4-oxopentanoyloxy)-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-3,4-dibenzoyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate

英文别名

——

methyl (2S,3S,4S,5R,6R)-3-[[(4aR,6S,7R,8R,8aS)-8-[(2R,3R,4S,5S,6S)-5-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-(4-oxopentanoyloxy)-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-3,4-dibenzoyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate化学式

CAS

1158797-06-8

化学式

C₉₈H₁₂₇Cl₉N₆O₃₄Si₃

mdl

——

分子量

2336.44

InChiKey

DJWKMJDIRPXRBZ-NZIHKPOOSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

15.34
重原子数：

150
可旋转键数：

43
环数：

12.0
sp3杂化的碳原子比例：

0.64
拓扑面积：

451
氢给体数：

3
氢受体数：

36

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
——	methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate	1158797-05-7	C₅₆H₇₇Cl₆N₅O₁₉Si₂	1393.14
——	methyl (phenyl 2,3-di-O-benzoyl-4-[4,6-O-di-tert-butylsilylidene-3-O-levulinoyl-2-N-trichloroacetamido-β-D-glucopyranosyl]-1-thio-β-D-glucopyranosyl uronate)	1158797-00-2	C₄₈H₅₆Cl₃NO₁₅SSi	1053.48

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6S,7R,8R,8aS)-6-[(2S,3S,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-dibenzoyloxy-2-methoxycarbonyloxan-3-yl]oxy-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate	1158797-07-9	C₉₃H₁₂₁Cl₉N₆O₃₂Si₃	2238.34

反应信息

作为反应物：

描述：

methyl (2S,3S,4S,5R,6R)-3-[[(4aR,6S,7R,8R,8aS)-8-[(2R,3R,4S,5S,6S)-5-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-(4-oxopentanoyloxy)-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-3,4-dibenzoyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate 在吡啶、一水合肼、溶剂黄146 作用下，反应 0.5h，以91%的产率得到methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6S,7R,8R,8aS)-6-[(2S,3S,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-dibenzoyloxy-2-methoxycarbonyloxan-3-yl]oxy-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate

参考文献：

名称：

Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

摘要：

An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

DOI：

10.1021/jo9003713
作为产物：

描述：

methyl (phenyl 2,3-di-O-benzoyl-4-[4,6-O-di-tert-butylsilylidene-3-O-levulinoyl-2-N-trichloroacetamido-β-D-glucopyranosyl]-1-thio-β-D-glucopyranosyl uronate) 、 methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate 在 N-碘代丁二酰亚胺、三氟甲磺酸作用下，以二氯甲烷为溶剂，反应 2.5h，以98%的产率得到methyl (2S,3S,4S,5R,6R)-3-[[(4aR,6S,7R,8R,8aS)-8-[(2R,3R,4S,5S,6S)-5-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-(4-oxopentanoyloxy)-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-3,4-dibenzoyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate

参考文献：

名称：

Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

摘要：

An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

DOI：

10.1021/jo9003713

点击查看最新优质反应信息

文献信息

Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

作者：Jasper Dinkelaar、Henrik Gold、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

DOI：10.1021/jo9003713

日期：2009.6.5

An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

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