(2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester

Base Information

• Chemical Name: (2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester
• CAS No.: 214261-11-7
• Molecular Formula: C₄₁H₅₂O₆
• Molecular Weight: 640.86

Synonyms:(2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester

Chemical Property of (2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester

There total 17 articles about (2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester 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:

(3S,5E)-6-iodo-3,5-dimethyl-5-hexen-1-ol (214260-98-7) → (2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester (214261-11-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 - -60 deg C, 30 in, 2.) CH₂Cl₂, -60 deg C to rt

2: 99 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

3: NH₂OH*HCl, KOH / dimethylformamide; ethyl acetate / 3 h / 100 °C

4: 0.547 g / aq. HCl / tetrahydrofuran / 3 h / Heating

5: 99 percent / toluene / 4 h / 80 °C

6: 1.) CaCO₃, 4 Angstroem MS / 1.) PhMe, 40 deg C, 4 h, 2.) PhMe, 80 deg C, 18 h

7: 89 percent / DIBALH / toluene / 2 h / -78 °C

8: 100 percent / pyridine / 70 °C

9: 84 percent / Ag₂CO₃, Et₃N, Pd(OAc)2 / CH₂Cl₂; ethanol / 3 h

10: m-CPBA / diethyl ether / 1 h / Ambient temperature

11: 1.) aq. HCl, 2.) NaH₂PO₄, NaClO₂, 2-methyl-2-butene / 1.) THF, rt, 30 min, 2.) t-BuOH, H₂O, rt, 1 h

With hydrogenchloride; palladium diacetate; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; 4 Angstroem MS; hydroxylamine hydrochloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; silver carbonate; calcium carbonate; In tetrahydrofuran; pyridine; diethyl ether; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo980813u

Reference yield:

(S)-3-methylhex-5-yn-1-ol (214260-97-6) → (2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester (214261-11-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) Cp₂ZrCl₂, 2.) I₂ / 1.) ClH₂CH₂Cl, rt, 24 h, 2.) ClCH₂CH₂Cl, THF_. -20 deg C, 2 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 - -60 deg C, 30 in, 2.) CH₂Cl₂, -60 deg C to rt

3: 99 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

4: NH₂OH*HCl, KOH / dimethylformamide; ethyl acetate / 3 h / 100 °C

5: 0.547 g / aq. HCl / tetrahydrofuran / 3 h / Heating

6: 99 percent / toluene / 4 h / 80 °C

7: 1.) CaCO₃, 4 Angstroem MS / 1.) PhMe, 40 deg C, 4 h, 2.) PhMe, 80 deg C, 18 h

8: 89 percent / DIBALH / toluene / 2 h / -78 °C

9: 100 percent / pyridine / 70 °C

10: 84 percent / Ag₂CO₃, Et₃N, Pd(OAc)2 / CH₂Cl₂; ethanol / 3 h

11: m-CPBA / diethyl ether / 1 h / Ambient temperature

12: 1.) aq. HCl, 2.) NaH₂PO₄, NaClO₂, 2-methyl-2-butene / 1.) THF, rt, 30 min, 2.) t-BuOH, H₂O, rt, 1 h

With hydrogenchloride; palladium diacetate; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; zirconocene dichloride; 2-methyl-but-2-ene; oxalyl dichloride; 4 Angstroem MS; hydroxylamine hydrochloride; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; silver carbonate; calcium carbonate; In tetrahydrofuran; pyridine; diethyl ether; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo980813u

Reference yield:

(4R,2''RS)-4-methyl-6-(2-tetrahydropyranyloxy)1-hexyne (214260-96-5) → (2E,4E)-(7R,12R,13R)-12-Hydroxy-3,5,7-trimethyl-13-trityloxymethyl-tetradeca-2,4-dienedioic acid 1-tert-butyl ester (214261-11-7)

Guidance literature:

Multi-step reaction with 13 steps

1: CSA / methanol / 1 h / Ambient temperature

2: 1.) Cp₂ZrCl₂, 2.) I₂ / 1.) ClH₂CH₂Cl, rt, 24 h, 2.) ClCH₂CH₂Cl, THF_. -20 deg C, 2 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 - -60 deg C, 30 in, 2.) CH₂Cl₂, -60 deg C to rt

4: 99 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

5: NH₂OH*HCl, KOH / dimethylformamide; ethyl acetate / 3 h / 100 °C

6: 0.547 g / aq. HCl / tetrahydrofuran / 3 h / Heating

7: 99 percent / toluene / 4 h / 80 °C

8: 1.) CaCO₃, 4 Angstroem MS / 1.) PhMe, 40 deg C, 4 h, 2.) PhMe, 80 deg C, 18 h

9: 89 percent / DIBALH / toluene / 2 h / -78 °C

10: 100 percent / pyridine / 70 °C

11: 84 percent / Ag₂CO₃, Et₃N, Pd(OAc)2 / CH₂Cl₂; ethanol / 3 h

12: m-CPBA / diethyl ether / 1 h / Ambient temperature

13: 1.) aq. HCl, 2.) NaH₂PO₄, NaClO₂, 2-methyl-2-butene / 1.) THF, rt, 30 min, 2.) t-BuOH, H₂O, rt, 1 h

With hydrogenchloride; palladium diacetate; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; zirconocene dichloride; 2-methyl-but-2-ene; oxalyl dichloride; 4 Angstroem MS; camphor-10-sulfonic acid; hydroxylamine hydrochloride; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; silver carbonate; calcium carbonate; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo980813u

upstream raw materials:

(S)-3-methylhex-5-yn-1-ol

(3S,5E)-6-iodo-3,5-dimethyl-5-hexenal

(E)-(S)-1,6-Diiodo-2,4-dimethyl-hex-1-ene

(3S,5E)-6-iodo-3,5-dimethyl-5-hexen-1-ol

Downstream raw materials:

(2E,4E)-(R)-3,5,7-Trimethyl-11-((2R,3R)-4-oxo-3-trityloxymethyl-oxetan-2-yl)-undeca-2,4-dienoic acid tert-butyl ester

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