methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

Base Information

Chemical Name:methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate
CAS No.:385443-75-4
Molecular Formula:C₄₂H₈₀O₈Si₃
Molecular Weight:797.349
Hs Code.:

methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

Synonyms:methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

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Chemical Property of methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

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Technology Process of methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

There total 19 articles about methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate 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: 84.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 385443-59-4
methyl (2R,3S,4S,5R,6S,7R,8E,10S)-7,11-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2,3-dihydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

: 385443-75-4
methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 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

: 385443-75-4
methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

Guidance literature:: Multi-step reaction with 13 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: 14.5 g / imidazole / dimethylformamide / 120 h / 20 °C

9: 47 percent / DIBAH / hexane; CH₂Cl₂ / 3 h / -30 °C

10: 1.13 g / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h

11: 1.02 g / benzene / 18 h / 20 °C

12: 68 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 60 h / 20 °C

13: 84 percent / imidazole / dimethylformamide / 5 h / 0 °C

With 1H-imidazole; AD-mix-α; tin(II) trifluoromethanesulfonate; oxalyl dichloride; methanesulfonamide; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1: Swern oxidation / 2: Wittig reaction / 4: Swern oxidation / 10: Dess-Martin oxidation / 11: Wittig reaction;
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

: 385443-75-4
methyl (2R,3S,4S,5R,6S,7R,8E,10S)-2,7,11-tris[(1,1-dimethylethyl)dimethylsilyloxy]-3-hydroxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate

Guidance literature:: Multi-step reaction with 12 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: 14.5 g / imidazole / dimethylformamide / 120 h / 20 °C

8: 47 percent / DIBAH / hexane; CH₂Cl₂ / 3 h / -30 °C

9: 1.13 g / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h

10: 1.02 g / benzene / 18 h / 20 °C

11: 68 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 60 h / 20 °C

12: 84 percent / imidazole / dimethylformamide / 5 h / 0 °C

With 1H-imidazole; AD-mix-α; tin(II) trifluoromethanesulfonate; oxalyl dichloride; methanesulfonamide; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1: Wittig reaction / 3: Swern oxidation / 9: Dess-Martin oxidation / 10: Wittig reaction;
DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P