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

Base Information

Chemical Name:methyl (2R,3S,4R,5S,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-3,5-(4-methoxybenzylidenedioxy)-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-undecenoate
CAS No.:385443-52-7
Molecular Formula:C₃₄H₅₈O₁₀Si
Molecular Weight:654.914
Hs Code.:

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

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

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

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

There total 20 articles about methyl (2R,3S,4R,5S,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-3,5-(4-methoxybenzylidenedioxy)-2,7-bis(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:

: 107-30-2
chloromethyl methyl ether

: 385443-68-5
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

: 385443-52-7
methyl (2R,3S,4R,5S,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-3,5-(4-methoxybenzylidenedioxy)-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-undecenoate

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 20h;
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

: 385443-52-7
methyl (2R,3S,4R,5S,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-3,5-(4-methoxybenzylidenedioxy)-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-undecenoate

Guidance literature:: Multi-step reaction with 14 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

12: 86 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 - 20 °C

13: 372 mg / DDQ / CH₂Cl₂ / 0.5 h / -30 °C

14: 250 mg / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

With pyridine; AD-mix-α; tin(II) trifluoromethanesulfonate; oxalyl dichloride; methanesulfonamide; tetra-(n-butyl)ammonium iodide; 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; water; tert-butyl alcohol; 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:

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

: 385443-52-7
methyl (2R,3S,4R,5S,6S,7R,8E,10S)-11-[(1,1-dimethylethyl)dimethylsilyloxy]-3,5-(4-methoxybenzylidenedioxy)-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-undecenoate

Guidance literature:: Multi-step reaction with 13 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

11: 86 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 - 20 °C

12: 372 mg / DDQ / CH₂Cl₂ / 0.5 h / -30 °C

13: 250 mg / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

With pyridine; AD-mix-α; tin(II) trifluoromethanesulfonate; oxalyl dichloride; methanesulfonamide; tetra-(n-butyl)ammonium iodide; 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; water; tert-butyl alcohol; 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