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举例 :可输入Filippa Pettersson 或者 Cancer Res. 75(6) , 1102-12, (2015) 或者10.1002/anie.201600521

Total synthesis of 6-deoxy-6-aminoheptopyranuronic acid derivatives

G Casiraghi, L Colombo, G Rassu…

文献索引：Casiraghi, Giovanni; Colombo, Lino; Rassu, Gloria; Spanu, Pietro Journal of Organic Chemistry, 1991 , vol. 56, # 23 p. 6523 - 6527

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被引用次数: 86

摘要

Two enantio couples of terminal C-glycopyranosyl a-amino acids, namely the aminopyranuronic acids L-9, D-9 and L-10, D-10, have been synthesized from the serine- derived pair L-2, D-2 by exploiting enantiomerically pure butenolide intermediates 3 and 4. The key synthetic steps involved the sequential antiselective cis dihydroxylation of the butenolide double bond and the clean furanose-to-pyranose ring expansion to construct ...

(S)-(-)-3-(叔丁氧羰基)-4-甲酰-2,2-二甲基-1,3-噁唑烷结构式

(S)-(-)-3-(叔丁氧羰...

~%

1,2,3,4-Tetra-O-acetyl-5-(2,2-dimethyl-3-{[(2-methyl-2-propanyl)o xy]carbonyl}-1,3-oxazolidin-4-yl)pentopyranose结构式

1,2,3,4-Tetra-O...

tert-butyl (4S)-4-[(S)-hydroxy-[(2S)-5-oxo-2H-furan-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate结构式

tert-butyl (4S)...

~%

1,2,3,4-Tetra-O-acetyl-5-(2,2-dimethyl-3-{[(2-methyl-2-propanyl)o xy]carbonyl}-1,3-oxazolidin-4-yl)pentopyranose结构式

1,2,3,4-Tetra-O...

tert-butyl (4S)-4-[(R)-hydroxy-[(2R)-5-oxo-2H-furan-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate结构式

tert-butyl (4S)...

~%

1,2,3,4-Tetra-O-acetyl-5-(2,2-dimethyl-3-{[(2-methyl-2-propanyl)o xy]carbonyl}-1,3-oxazolidin-4-yl)pentopyranose结构式

1,2,3,4-Tetra-O...

未登录结构式

~%

1,2,3,4-Tetra-O-acetyl-5-(2,2-dimethyl-3-{[(2-methyl-2-propanyl)o xy]carbonyl}-1,3-oxazolidin-4-yl)pentopyranose结构式

1,2,3,4-Tetra-O...

2-Methyl-2-propanyl 2,2-dimethyl-4-({5-oxo-3,4-bis[(trimethylsily l)oxy]tetrahydro-2-furanyl}[(trimethylsilyl)oxy]methyl)-1,3-oxazo lidine-3-carboxylate (non-preferred name)结构式

2-Methyl-2-prop...

~%

1,2,3,4-Tetra-O-acetyl-5-(2,2-dimethyl-3-{[(2-methyl-2-propanyl)o xy]carbonyl}-1,3-oxazolidin-4-yl)pentopyranose结构式

1,2,3,4-Tetra-O...

(R)-(+)-3-Boc-2,2-二甲基噁唑啉-4-甲醛结构式

(R)-(+)-3-Boc-2...

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

6,7-N,O-Isopropylidene-6-[(tert-butoxycarbonyl)amino]-2,3,6-trideoxy-D-ribo-hept-2-enono-1,4-lactone结构式

6,7-N,O-Isoprop...

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

tert-butyl (4R)-4-[(R)-hydroxy-[(2R)-5-oxo-2H-furan-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate结构式

tert-butyl (4R)...

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

(S)-tert-butyl 2,2-dimethyl-4-((2S,3S,4R,5R,6R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)oxazolidine-3-carboxylate结构式

(S)-tert-butyl ...

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

tert-butyl (4S)-4-((1S)-((2R,3R,4R)-5-hydroxy-3,4-bis((trimethylsilyl)oxy)tetrahydrofuran-2-yl)((trimethylsilyl)oxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate结构式

tert-butyl (4S)...

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

tert-butyl 2,2-dimethyl-4-[(R)-[(2S,3S,4S)-5-oxo-3,4-bis(trimethylsilyloxy)oxolan-2-yl]-trimethylsilyloxymethyl]-1,3-oxazolidine-3-carboxylate结构式

tert-butyl 2,2-...

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

6-deoxy-6-tert-butoxycarbonylamino-α-D-glycero-D-talo-heptopyranose tetraacetate结构式

6-deoxy-6-tert-...

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

未登录结构式

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

重氮甲烷结构式

1,2,3,4-tetra-O-acetyl-6-deoxy-6-tert-butoxycarbonylamino-α-D-glycero-D-talo-heptopyranuronic acid结构式

1,2,3,4-tetra-O...

~%

methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2R,3R,4R,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]acetate结构式

methyl (2S)-2-[...

(S)-(-)-3-(叔丁氧羰基)-4-甲酰-2,2-二甲基-1,3-噁唑烷结构式

(S)-(-)-3-(叔丁氧羰...

~%

2-Methyl-2-propanyl 2,2-dimethyl-4-({5-oxo-3,4-bis[(trimethylsily l)oxy]tetrahydro-2-furanyl}[(trimethylsilyl)oxy]methyl)-1,3-oxazo lidine-3-carboxylate (non-preferred name)结构式

2-Methyl-2-prop...

tert-butyl (4S)-4-[(S)-hydroxy-[(2S)-5-oxo-2H-furan-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate结构式

tert-butyl (4S)...

~%

2-Methyl-2-propanyl 2,2-dimethyl-4-({5-oxo-3,4-bis[(trimethylsily l)oxy]tetrahydro-2-furanyl}[(trimethylsilyl)oxy]methyl)-1,3-oxazo lidine-3-carboxylate (non-preferred name)结构式

2-Methyl-2-prop...

tert-butyl (4S)-4-[(R)-hydroxy-[(2R)-5-oxo-2H-furan-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate结构式

tert-butyl (4S)...

~%

2-Methyl-2-propanyl 2,2-dimethyl-4-({5-oxo-3,4-bis[(trimethylsily l)oxy]tetrahydro-2-furanyl}[(trimethylsilyl)oxy]methyl)-1,3-oxazo lidine-3-carboxylate (non-preferred name)结构式

2-Methyl-2-prop...

未登录结构式

~%

2-Methyl-2-propanyl 2,2-dimethyl-4-({5-oxo-3,4-bis[(trimethylsily l)oxy]tetrahydro-2-furanyl}[(trimethylsilyl)oxy]methyl)-1,3-oxazo lidine-3-carboxylate (non-preferred name)结构式

2-Methyl-2-prop...