(2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol

Base Information

Chemical Name:(2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol
CAS No.:385443-54-9
Molecular Formula:C₂₇H₄₈O₅Si
Molecular Weight:480.761
Hs Code.:

Synonyms:(2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol

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Chemical Property of (2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol

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Technology Process of (2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol

There total 12 articles about (2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol 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: 3.26%

: 385443-62-9
(2S,4R,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-5-hydroxy-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonen-3-one

: 385443-54-9
(2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P

Reference yield:

: 105859-45-8
(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol

: 385443-54-9
(2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 10 g / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

2: 12.2 g / CH₂Cl₂ / 20 h / 20 °C

3: 5.2 g / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

4: 2.59 g / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

5: 4.0 g / Sn(OTf)2; iPr₂EtN / CH₂Cl₂ / 12 h / 20 °C

6: 3.26 percent / DIBAH / hexane; tetrahydrofuran / 2 h / -78 °C

With tin(II) trifluoromethanesulfonate; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 1: Swern oxidation / 2: Wittig reaction / 4: Swern oxidation;
DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P

Reference yield:

: 97826-89-6
(2R)-3-(tert-butyldimethylsilyloxy)-2-methylpropanal

: 385443-54-9
(2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-1-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-6-nonene-3,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 12.2 g / CH₂Cl₂ / 20 h / 20 °C

2: 5.2 g / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

3: 2.59 g / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

4: 4.0 g / Sn(OTf)2; iPr₂EtN / CH₂Cl₂ / 12 h / 20 °C

5: 3.26 percent / DIBAH / hexane; tetrahydrofuran / 2 h / -78 °C

With tin(II) trifluoromethanesulfonate; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 1: Wittig reaction / 3: Swern oxidation;
DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P