3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose

Base Information

Chemical Name:3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose
CAS No.:170873-33-3
Molecular Formula:C₄₇H₉₀ClNO₁₁SeSi₄
Molecular Weight:1071.99
Hs Code.:

3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose

Synonyms:3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose

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Chemical Property of 3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose

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Technology Process of 3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose

There total 15 articles about 3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

: 51694-22-5
ortho-nitrophenyl selenocyanate

: 170873-22-0
3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-7-C-(hydroxymethyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-α-D-gluco-L-ido-undecofuranose

: 170873-33-3
3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose

Guidance literature:: With tributylphosphine; In tetrahydrofuran; at 50 ℃; for 1h;
DOI:10.1021/jo00123a021

Reference yield:

: 170872-96-5
(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

: 170873-33-3
3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose

Guidance literature:: Multi-step reaction with 10 steps

1: NaBH₃CN / 2 h / 0 °C

2: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: 78 percent / Bu₃SnH, AIBN / toluene / 2 h / 80 °C

4: 88 percent / DIBAH / CH₂Cl₂ / 0.5 h / -65 °C

5: n-BuLi, (Me₃Si)2NH / tetrahydrofuran; hexane / -65 °C

6: 84 percent / MeONa / tetrahydrofuran; methanol / 0.17 h / -20 °C

7: 66 percent / NaBH₄ / methanol / 0.17 h / 0 °C

8: 91 percent / pyridine / 18 h / 20 °C

9: 77 percent / DIBAH / toluene / 0.5 h / -65 °C

10: 76 percent / Bu₃P / tetrahydrofuran / 1 h / 50 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributylphosphine; tri-n-butyl-tin hydride; sodium methylate; diisobutylaluminium hydride; sodium cyanoborohydride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/jo00123a021

Reference yield:

: 170872-97-6
3-O-(tert-Butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose

: 170873-33-3
3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: n-BuLi, (Me₃Si)2NH / tetrahydrofuran; hexane / -65 °C

2: 84 percent / MeONa / tetrahydrofuran; methanol / 0.17 h / -20 °C

3: 66 percent / NaBH₄ / methanol / 0.17 h / 0 °C

4: 91 percent / pyridine / 18 h / 20 °C

5: 77 percent / DIBAH / toluene / 0.5 h / -65 °C

6: 76 percent / Bu₃P / tetrahydrofuran / 1 h / 50 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; tributylphosphine; sodium methylate; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; hexane; toluene;
DOI:10.1021/jo00123a021