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

Base Information

• Chemical Name: methyl (2R,3S,4R,5R,6S,7R,8E,10S)-2,7-bis[(1,1-dimethylethyl)dimethylsilyloxy]-3-methoxy-5-(4-methoxybenzyloxy)-11-oxo-4,6,8,10-tetramethyl-8-undecenoate
• CAS No.: 385443-77-6
• Molecular Formula: C₃₇H₆₆O₈Si₂
• Molecular Weight: 695.097

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about methyl (2R,3S,4R,5R,6S,7R,8E,10S)-2,7-bis[(1,1-dimethylethyl)dimethylsilyloxy]-3-methoxy-5-(4-methoxybenzyloxy)-11-oxo-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:

methyl (2R,3S,4R,5R,6S,7R,8E,10S)-2,7-bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-hydroxy-3-methoxy-5-(4-methoxybenzyloxy)-4,6,8,10-tetramethyl-8-undecenoate (385443-76-5) → methyl (2R,3S,4R,5R,6S,7R,8E,10S)-2,7-bis[(1,1-dimethylethyl)dimethylsilyloxy]-3-methoxy-5-(4-methoxybenzyloxy)-11-oxo-4,6,8,10-tetramethyl-8-undecenoate (385443-77-6)

Guidance literature:

With sodium hydrogencarbonate; 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:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → methyl (2R,3S,4R,5R,6S,7R,8E,10S)-2,7-bis[(1,1-dimethylethyl)dimethylsilyloxy]-3-methoxy-5-(4-methoxybenzyloxy)-11-oxo-4,6,8,10-tetramethyl-8-undecenoate (385443-77-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 92 percent / pyridinium p-toluenesulfonare / CH₂Cl₂ / 19 h / 20 °C

2: 5.6 g / iPrMgBr / tetrahydrofuran / 0.67 h / -20 - -10 °C

3: 4.38 g / tetrahydrofuran / 1 h / 0 °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

13: 92 percent / 1,8-bis(dimethylamino)naphthalene / CH₂Cl₂ / 40 h / 20 °C

14: 85 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 3 h / 0 °C

15: 370 mg / Dess-Marti periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; AD-mix-α; tin(II) trifluoromethanesulfonate; methanesulfonamide; camphor-10-sulfonic acid; isopropylmagnesium bromide; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 9: Dess-Martin oxidation / 10: Wittig reaction / 15: Dess-Martin oxidation;

DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P

Reference yield:

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate (132969-71-2) → methyl (2R,3S,4R,5R,6S,7R,8E,10S)-2,7-bis[(1,1-dimethylethyl)dimethylsilyloxy]-3-methoxy-5-(4-methoxybenzyloxy)-11-oxo-4,6,8,10-tetramethyl-8-undecenoate (385443-77-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 5.6 g / iPrMgBr / tetrahydrofuran / 0.67 h / -20 - -10 °C

2: 4.38 g / tetrahydrofuran / 1 h / 0 °C

3: 4.0 g / Sn(OTf)2; iPr₂EtN / CH₂Cl₂ / 12 h / 20 °C

4: 3.26 percent / DIBAH / hexane; tetrahydrofuran / 2 h / -78 °C

5: 450 mg / DDQ / CH₂Cl₂ / 4 h / 0 °C

6: 14.5 g / imidazole / dimethylformamide / 120 h / 20 °C

7: 47 percent / DIBAH / hexane; CH₂Cl₂ / 3 h / -30 °C

8: 1.13 g / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.33 h

9: 1.02 g / benzene / 18 h / 20 °C

10: 68 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 60 h / 20 °C

11: 84 percent / imidazole / dimethylformamide / 5 h / 0 °C

12: 92 percent / 1,8-bis(dimethylamino)naphthalene / CH₂Cl₂ / 40 h / 20 °C

13: 85 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 3 h / 0 °C

14: 370 mg / Dess-Marti periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; AD-mix-α; tin(II) trifluoromethanesulfonate; methanesulfonamide; camphor-10-sulfonic acid; isopropylmagnesium bromide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 8: Dess-Martin oxidation / 9: Wittig reaction / 14: Dess-Martin oxidation;

DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P

upstream raw materials:

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

O-(4-methoxybenzyl)-trichloroacetimidate

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one

Downstream raw materials:

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

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