Dodecanoic acid, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, methyl ester, (3S,4S,6S,8R,10S,11R)-

Base Information

• Chemical Name: Dodecanoic acid, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, methyl ester, (3S,4S,6S,8R,10S,11R)-
• CAS No.: 501419-14-3
• Molecular Formula: C28H48O7
• Molecular Weight: 496.685

Synonyms:

Chemical Property of Dodecanoic acid, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, methyl ester, (3S,4S,6S,8R,10S,11R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Dodecanoic acid, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, methyl ester, (3S,4S,6S,8R,10S,11R)-

There total 27 articles about Dodecanoic acid, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, methyl ester, (3S,4S,6S,8R,10S,11R)- 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:

(+)-(2S,3R)-4-benzyloxy-3-(tert-butyldimethylsiloxy)-2-methylbutan-1-ol (501419-25-6) → 3S,11R-bis-methoxymethoxy-4S,6S,8R,10S-tetramethyl-12-benzyloxy-dodecanoic acid methyl ester (501419-14-3)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 96 percent / triphenylphosphine; iodine; imidazole / acetonitrile; diethyl ether / 20 °C

2.1: LiCl; diisopropylamine; n-butyllithium / tetrahydrofuran; petroleum ether / 1.33 h / -78 - 20 °C

2.2: 93 percent / tetrahydrofuran; various solvent(s) / 40 h / 0 °C

3.1: 93 percent / diisopropylamine; n-butyllithium; borane-ammonium complex / tetrahydrofuran; petroleum ether / 2.17 h / 0 - 20 °C

4.1: 95 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 0.17 h / 20 °C

5.1: tert-butyllithium; ZnCl₂ / diethyl ether; petroleum ether / 1 h / 20 °C

5.2: 58 percent / Pd(PPh₃)4 / diethyl ether; various solvent(s) / 16 h

6.1: 87 percent / TBAF / tetrahydrofuran / 20 h / 20 °C

7.1: 86 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 4 h / 36201.3 Torr

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

9.1: 93 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C / pH 7

10.1: triethylamine / CH₂Cl₂ / 1.5 h / 20 °C

11.1: HF / acetonitrile / 3 h / 20 °C

12.1: 98 percent / potassium carbonate / methanol / 0.75 h

13.1: 92 percent / lithium perchlorate / acetonitrile / 24 h / 70 °C

14.1: 81 percent / diisopropylethylamine / CH₂Cl₂ / 28 h / 20 °C

15.1: DIBAL-H / CH₂Cl₂; petroleum ether / 1 h / -78 °C

16.1: 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 1 h / 0 °C

17.1: K₂CO₃ / dimethylformamide / 3.5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; lithium perchlorate; diisobutylaluminium hydride; potassium carbonate; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; zinc(II) chloride; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; Petroleum ether; tert-butyl alcohol; 2.1: Myer's alkylation / 5.2: Negishi coupling;

DOI:10.1021/ja028941u

Reference yield:

(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-[(4-methoxybenzyl)oxy]-2-methylbutan-1-ol (501419-20-1) → 3S,11R-bis-methoxymethoxy-4S,6S,8R,10S-tetramethyl-12-benzyloxy-dodecanoic acid methyl ester (501419-14-3)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

2.1: 94 percent / triphenylphosphine / CH₂Cl₂ / 0.67 h / -78 - 0 °C

3.1: n-butyllithium / tetrahydrofuran; petroleum ether / 1 h / -25 °C

3.2: 97 percent / tetrahydrofuran; various solvent(s) / 1 h / 20 °C

4.1: Cp₂ZrHCl / CH₂Cl₂ / 2 h

4.2: 89 percent / I₂ / CH₂Cl₂; CCl₄

5.1: tert-butyllithium; ZnCl₂ / diethyl ether; petroleum ether / 1 h / 20 °C

5.2: 58 percent / Pd(PPh₃)4 / diethyl ether; various solvent(s) / 16 h

6.1: 87 percent / TBAF / tetrahydrofuran / 20 h / 20 °C

7.1: 86 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 4 h / 36201.3 Torr

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

9.1: 93 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C / pH 7

10.1: triethylamine / CH₂Cl₂ / 1.5 h / 20 °C

11.1: HF / acetonitrile / 3 h / 20 °C

12.1: 98 percent / potassium carbonate / methanol / 0.75 h

13.1: 92 percent / lithium perchlorate / acetonitrile / 24 h / 70 °C

14.1: 81 percent / diisopropylethylamine / CH₂Cl₂ / 28 h / 20 °C

15.1: DIBAL-H / CH₂Cl₂; petroleum ether / 1 h / -78 °C

16.1: 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 1 h / 0 °C

17.1: K₂CO₃ / dimethylformamide / 3.5 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; Schwartz's reagent; n-butyllithium; 2-methyl-but-2-ene; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; lithium perchlorate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; Petroleum ether; tert-butyl alcohol; 3.1: Corey-Fuchs reaction / 5.2: Negishi coupling;

DOI:10.1021/ja028941u

Reference yield:

4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid methyl ester (501419-24-5) → 3S,11R-bis-methoxymethoxy-4S,6S,8R,10S-tetramethyl-12-benzyloxy-dodecanoic acid methyl ester (501419-14-3)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 94 percent / DIBAL-H / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2.1: 96 percent / triphenylphosphine; iodine; imidazole / acetonitrile; diethyl ether / 20 °C

3.1: LiCl; diisopropylamine; n-butyllithium / tetrahydrofuran; petroleum ether / 1.33 h / -78 - 20 °C

3.2: 93 percent / tetrahydrofuran; various solvent(s) / 40 h / 0 °C

4.1: 93 percent / diisopropylamine; n-butyllithium; borane-ammonium complex / tetrahydrofuran; petroleum ether / 2.17 h / 0 - 20 °C

5.1: 95 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 0.17 h / 20 °C

6.1: tert-butyllithium; ZnCl₂ / diethyl ether; petroleum ether / 1 h / 20 °C

6.2: 58 percent / Pd(PPh₃)4 / diethyl ether; various solvent(s) / 16 h

7.1: 87 percent / TBAF / tetrahydrofuran / 20 h / 20 °C

8.1: 86 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 4 h / 36201.3 Torr

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

10.1: 93 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C / pH 7

11.1: triethylamine / CH₂Cl₂ / 1.5 h / 20 °C

12.1: HF / acetonitrile / 3 h / 20 °C

13.1: 98 percent / potassium carbonate / methanol / 0.75 h

14.1: 92 percent / lithium perchlorate / acetonitrile / 24 h / 70 °C

15.1: 81 percent / diisopropylethylamine / CH₂Cl₂ / 28 h / 20 °C

16.1: DIBAL-H / CH₂Cl₂; petroleum ether / 1 h / -78 °C

17.1: 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 1 h / 0 °C

18.1: K₂CO₃ / dimethylformamide / 3.5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; lithium perchlorate; diisobutylaluminium hydride; potassium carbonate; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; zinc(II) chloride; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; Petroleum ether; tert-butyl alcohol; 3.1: Myer's alkylation / 6.2: Negishi coupling;

DOI:10.1021/ja028941u

upstream raw materials:

C₂₇H₄₆O₇

methyl iodide

(+)-(2S,3R)-4-benzyloxy-3-(tert-butyldimethylsiloxy)-2-methylbutan-1-ol

4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid methyl ester

Downstream raw materials:

borrelidin

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