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

Base Information

Chemical Name: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
CAS No.:385443-71-0
Molecular Formula:C₂₉H₄₆O₁₀
Molecular Weight:554.678
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 19 articles about 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 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:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 385443-71-0
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

Guidance literature:: Multi-step reaction with 16 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: 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

14: 93 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

15: 200 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

16: 73 mg / diethyl ether / 1 h / -78 °C

With pyridine; AD-mix-α; tin(II) trifluoromethanesulfonate; methanesulfonamide; tetrabutyl ammonium fluoride; isopropylmagnesium bromide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 9: Dess-Martin oxidation / 15: Dess-Martin oxidation;
DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P

Reference yield:

: 132969-71-2
methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

: 385443-71-0
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

Guidance literature:: Multi-step reaction with 15 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: 500 mg / iPr₂NEt / CH₂Cl₂ / 40 h / 20 °C

7: 330 mg / DIBAH / hexane; CH₂Cl₂ / 2 h / -30 °C

8: 150 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

9: 155 mg / benzene / 25 h / 20 °C

10: 86 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 - 20 °C

11: 372 mg / DDQ / CH₂Cl₂ / 0.5 h / -30 °C

12: 250 mg / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

13: 93 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

14: 200 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

15: 73 mg / diethyl ether / 1 h / -78 °C

With pyridine; AD-mix-α; tin(II) trifluoromethanesulfonate; methanesulfonamide; tetrabutyl ammonium fluoride; isopropylmagnesium bromide; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 8: Dess-Martin oxidation / 14: Dess-Martin oxidation;
DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P

Reference yield:

: 182193-69-7
(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one

: 385443-71-0
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

Guidance literature:: Multi-step reaction with 13 steps

1: 4.0 g / Sn(OTf)2; iPr₂EtN / CH₂Cl₂ / 12 h / 20 °C

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

3: 450 mg / DDQ / CH₂Cl₂ / 4 h / 0 °C

4: 500 mg / iPr₂NEt / CH₂Cl₂ / 40 h / 20 °C

5: 330 mg / DIBAH / hexane; CH₂Cl₂ / 2 h / -30 °C

6: 150 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

7: 155 mg / benzene / 25 h / 20 °C

8: 86 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 - 20 °C

9: 372 mg / DDQ / CH₂Cl₂ / 0.5 h / -30 °C

10: 250 mg / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

11: 93 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

12: 200 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

13: 73 mg / diethyl ether / 1 h / -78 °C

With pyridine; AD-mix-α; tin(II) trifluoromethanesulfonate; methanesulfonamide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 6: Dess-Martin oxidation / 12: Dess-Martin oxidation;
DOI:10.1002/1099-0690(200110)2001:19<3615::AID-EJOC3615>3.0.CO;2-P