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

Base Information

Chemical Name:(2R,3S,4R,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-3-(4-methoxybenzyloxy)-5-methoxymethoxy-2,4,6,8-tetramethyl-6-nonenal
CAS No.:385443-66-3
Molecular Formula:C₂₉H₅₀O₆Si
Molecular Weight:522.798
Hs Code.:

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

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

There total 16 articles about (2R,3S,4R,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-3-(4-methoxybenzyloxy)-5-methoxymethoxy-2,4,6,8-tetramethyl-6-nonenal 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:

: 385443-57-2
(2S,3R,4S,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-3-(4-methoxybenzyloxy)-5-methoxymethoxy-2,4,6,8-tetramethyl-6-nonenol

: 385443-66-3
(2R,3S,4R,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-3-(4-methoxybenzyloxy)-5-methoxymethoxy-2,4,6,8-tetramethyl-6-nonenal

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;
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

: 385443-66-3
(2R,3S,4R,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-3-(4-methoxybenzyloxy)-5-methoxymethoxy-2,4,6,8-tetramethyl-6-nonenal

Guidance literature:: Multi-step reaction with 10 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

7: 450 mg / DDQ / CH₂Cl₂ / 4 h / 0 °C

8: 500 mg / iPr₂NEt / CH₂Cl₂ / 40 h / 20 °C

9: 330 mg / DIBAH / hexane; CH₂Cl₂ / 2 h / -30 °C

10: 150 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; tin(II) trifluoromethanesulfonate; oxalyl dichloride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; 1: Swern oxidation / 2: Wittig reaction / 4: Swern oxidation / 10: Dess-Martin 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

: 385443-66-3
(2R,3S,4R,5R,6E,8S)-9-[(1,1-dimethylethyl)dimethylsilyloxy]-3-(4-methoxybenzyloxy)-5-methoxymethoxy-2,4,6,8-tetramethyl-6-nonenal

Guidance literature:: Multi-step reaction with 9 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

6: 450 mg / DDQ / CH₂Cl₂ / 4 h / 0 °C

7: 500 mg / iPr₂NEt / CH₂Cl₂ / 40 h / 20 °C

8: 330 mg / DIBAH / hexane; CH₂Cl₂ / 2 h / -30 °C

9: 150 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; tin(II) trifluoromethanesulfonate; oxalyl dichloride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; 1: Wittig reaction / 3: Swern oxidation / 9: Dess-Martin oxidation;
DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P