(2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

Base Information

Chemical Name:(2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one
CAS No.:1335028-96-0
Molecular Formula:C₄₀H₆₀O₈Si
Molecular Weight:696.997
Hs Code.:

Synonyms:(2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

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Chemical Property of (2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

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Technology Process of (2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

There total 11 articles about (2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one 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: 99.0%

: 1335028-95-9
triethyl(((2R,3S)-1-((4-methoxybenzyl)oxy)-2-methylhex-5-yn-3-yl)oxy)silane

: 102716-67-6
(3R,6S)-3-(benzyloxy)-6-(((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)tetrahydro-2H-pyran-2-one

: 1335028-96-0
(2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

Guidance literature:: triethyl(((2R,3S)-1-((4-methoxybenzyl)oxy)-2-methylhex-5-yn-3-yl)oxy)silane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.666667h;

(3R,6S)-3-(benzyloxy)-6-(((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With water; ammonium chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1002/anie.201101741

Reference yield:

: 1335028-91-5
(2R,5S)-2-(benzyloxy)-7-methyloct-7-ene-1,5-diol

: 1335028-96-0
(2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 12 h

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 - -40 °C

2.2: 12 h / -40 - 25 °C

3.1: 1H-imidazole; dmap / dichloromethane / 3 h

4.1: AD-mix-β; water / tert-butyl alcohol / 24 h / 0 °C

5.1: pyridinium p-toluenesulfonate / dichloromethane / 2.5 h

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h

7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate / dichloromethane / 12 h

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C

8.2: 1 h / -78 °C

8.3: -78 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; AD-mix-β; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; toluene; tert-butyl alcohol; 4.1: Sharpless dihydroxylation;
DOI:10.1002/anie.201101741

Reference yield:

: (7R)-7-(benzyloxy)-8-((4-methoxybenzyl)oxy)-2-methyloct-1-en-4-ol

: 1335028-96-0
(2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 2 h / 25 °C / pH 7 / aq. buffer

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 12 h

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 - -40 °C

3.2: 12 h / -40 - 25 °C

4.1: 1H-imidazole; dmap / dichloromethane / 3 h

5.1: AD-mix-β; water / tert-butyl alcohol / 24 h / 0 °C

6.1: pyridinium p-toluenesulfonate / dichloromethane / 2.5 h

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h

8.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate / dichloromethane / 12 h

9.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C

9.2: 1 h / -78 °C

9.3: -78 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; AD-mix-β; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; toluene; tert-butyl alcohol; 5.1: Sharpless dihydroxylation;
DOI:10.1002/anie.201101741