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

Base Information

• Chemical Name: methyl (2E,4S,5R,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxybenzyloxy)-7-methoxymethoxy-4,6,8,10-tetramethyl-8-undecenoate
• CAS No.: 385443-67-4
• Molecular Formula: C₃₂H₅₄O₇Si
• Molecular Weight: 578.862

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about methyl (2E,4S,5R,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxybenzyloxy)-7-methoxymethoxy-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:

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol (105859-45-8) → methyl (2E,4S,5R,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxybenzyloxy)-7-methoxymethoxy-4,6,8,10-tetramethyl-8-undecenoate (385443-67-4)

Guidance literature:

Multi-step reaction with 11 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

11: 155 mg / benzene / 25 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; benzene; 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:

(2R)-3-(tert-butyldimethylsilyloxy)-2-methylpropanal (97826-89-6) → methyl (2E,4S,5R,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxybenzyloxy)-7-methoxymethoxy-4,6,8,10-tetramethyl-8-undecenoate (385443-67-4)

Guidance literature:

Multi-step reaction with 10 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

10: 155 mg / benzene / 25 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; benzene; 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

Reference yield:

methyl (R)-2-methyl-3-[(tert-butyldimethylsilyl)oxy]propionate (105859-44-7) → methyl (2E,4S,5R,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxybenzyloxy)-7-methoxymethoxy-4,6,8,10-tetramethyl-8-undecenoate (385443-67-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 18.6 g / LiBH₄ / diethyl ether / 5 h / Heating

2: 10 g / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

3: 12.2 g / CH₂Cl₂ / 20 h / 20 °C

4: 5.2 g / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

5: 2.59 g / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

6: 4.0 g / Sn(OTf)2; iPr₂EtN / CH₂Cl₂ / 12 h / 20 °C

7: 3.26 percent / DIBAH / hexane; tetrahydrofuran / 2 h / -78 °C

8: 450 mg / DDQ / CH₂Cl₂ / 4 h / 0 °C

9: 500 mg / iPr₂NEt / CH₂Cl₂ / 40 h / 20 °C

10: 330 mg / DIBAH / hexane; CH₂Cl₂ / 2 h / -30 °C

11: 150 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

12: 155 mg / benzene / 25 h / 20 °C

With pyridine; lithium borohydride; 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; diethyl ether; hexane; dichloromethane; benzene; 2: Swern oxidation / 3: Wittig reaction / 5: Swern oxidation / 11: Dess-Martin oxidation;

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

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

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

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol

(2R)-3-(tert-butyldimethylsilyloxy)-2-methylpropanal

Downstream raw materials:

methyl (2R,3S,4R,5S,6S,7R,8E,10S)-3,5-(4-methoxybenzylidenedioxy)-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-11-oxo-8-undecenoate

methyl (2R,3S,4R,5S,6S,7R,8E,10S)-11-hydroxy-3,5-(4-methoxybenzylidenedioxy)-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-undecenoate

methyl (2R,3S,4R,5S,6S,7R,8E,10S)-11-hydroxy-3,5-(4-methoxybenzylidenedioxy)-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-dodecenoate

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

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