(5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol

Base Information

Chemical Name:(5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol
CAS No.:1323140-53-9
Molecular Formula:C₂₆H₄₄O₄Si
Molecular Weight:448.718
Hs Code.:

Synonyms:(5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol

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Chemical Property of (5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol

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Technology Process of (5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol

There total 8 articles about (5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol 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: 94.0%

: 1323140-38-0
(8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-one

: 1323140-53-9
(5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol

Guidance literature:: With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at -30 ℃; for 1.58333h; optical yield given as %de;
DOI:10.1002/hlca.201000371

Reference yield:

: 33467-76-4
(E)-hept-2-en-1-ol

: 1323140-53-9
(5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: titanium(IV) isopropylate; Cumene hydroperoxide; D-(-)-diisopropyl tartrate / dichloromethane / -20 °C

2.1: tetrachloromethane; sodium hydrogencarbonate; triphenylphosphine / 3 h / Reflux

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.75 h / -40 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

5.2: 3 h / -78 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C / Inert atmosphere

7.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.58 h / -30 °C

With 1H-imidazole; titanium(IV) isopropylate; tetrachloromethane; n-butyllithium; Cumene hydroperoxide; dimethylsulfide borane complex; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; diisopropylamine; triphenylphosphine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1.1: Sharpless epoxidation;
DOI:10.1002/hlca.201000371

Reference yield:

: C₇H₁₃ClO

: 1323140-53-9
(5S,8R)-8-{[ (tert-butyl)dimethylsilyl]oxy}-1-[(4-methoxybenzyl)oxy]dodec-6-yn-5-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.75 h / -40 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

3.2: 3 h / -78 °C

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C / Inert atmosphere

5.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.58 h / -30 °C

With 1H-imidazole; n-butyllithium; dimethylsulfide borane complex; diisopropylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1002/hlca.201000371