(E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl ester
• CAS No.: 135708-93-9
• Molecular Formula: C₃₂H₆₄O₆Si₂
• Molecular Weight: 601.028
• Mol file: 135708-93-9.mol

Synonyms:(E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl ester

Chemical Property of (E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl ester

There total 19 articles about (E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl 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: 64.0%

(2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal (135708-92-8) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → (E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl ester (135708-93-9)

Guidance literature:

In toluene; at 80 ℃; for 36h;

DOI:10.1021/jo00020a026

Reference yield:

[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane (135708-75-7,135708-76-8) → (E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl ester (135708-93-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 1) O₃, pyridine, 2) DMS / 1) MeOH, CH₂Cl₂, -78 deg C, 2) r.t., 15 h

2: 2) 15percent aq.NaOH / 1) toluene, -78 deg C, 2 h, 2) r.t., 16 h

3: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

5: 1) 9-BBN, 2) 30percent H₂O₂, 3M NaOH / 1) THF, r.t., 4 h, 2) 0 deg C, 1 h

6: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

7: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

8: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

9: 1) LDA, HMPA / 1) THF, hexane, -78 deg C, 15 min, 2) THF, r.t., 0.5 h

10: toluene / 2 h / Heating

11: 0.1N aq.LiOH / tetrahydrofuran / 2 h

12: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 8 h

13: N-methylcarbazole, t-BuSH / aq. propan-2-ol / 2 h / Irradiation

14: 2) H₂ / 1) Raney-Ni, 2) PtO₂ / 1) EtOH, 30 min, 2) EtOAc, 45 min

15: H₂ / 10percent Pd-C / ethyl acetate / 6 h

16: 73 percent / RuCl₂(PPh₃)3 / benzene / 18 h / Ambient temperature

17: 64 percent / toluene / 36 h / 80 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium hydroxide; potassium permanganate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tris(triphenylphosphine)ruthenium(II) chloride; N-methylcarbazole; oxalyl dichloride; 2,3-dimercapto-succinic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; ozone; 2-methylpropan-2-thiol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; palladium on activated charcoal; nickel; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/jo00020a026

Reference yield:

(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene (89046-67-3,91796-47-3,91796-48-4,91798-02-6,91798-03-7,94233-73-5,94233-74-6,106357-32-8) → (E)-(4R,5S,7S,8R)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,4,8-trimethyl-non-2-enoic acid methyl ester (135708-93-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 98 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

2: 1) O₃, pyridine, 2) DMS / 1) MeOH, CH₂Cl₂, -78 deg C, 2) r.t., 15 h

3: 2) 15percent aq.NaOH / 1) toluene, -78 deg C, 2 h, 2) r.t., 16 h

4: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

6: 1) 9-BBN, 2) 30percent H₂O₂, 3M NaOH / 1) THF, r.t., 4 h, 2) 0 deg C, 1 h

7: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

8: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

9: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

10: 1) LDA, HMPA / 1) THF, hexane, -78 deg C, 15 min, 2) THF, r.t., 0.5 h

11: toluene / 2 h / Heating

12: 0.1N aq.LiOH / tetrahydrofuran / 2 h

13: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 8 h

14: N-methylcarbazole, t-BuSH / aq. propan-2-ol / 2 h / Irradiation

15: 2) H₂ / 1) Raney-Ni, 2) PtO₂ / 1) EtOH, 30 min, 2) EtOAc, 45 min

16: H₂ / 10percent Pd-C / ethyl acetate / 6 h

17: 73 percent / RuCl₂(PPh₃)3 / benzene / 18 h / Ambient temperature

18: 64 percent / toluene / 36 h / 80 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium hydroxide; potassium permanganate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tris(triphenylphosphine)ruthenium(II) chloride; N-methylcarbazole; oxalyl dichloride; 2,3-dimercapto-succinic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; ozone; 2-methylpropan-2-thiol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; palladium on activated charcoal; nickel; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/jo00020a026

upstream raw materials:

(2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal

methyl 2-(triphenylphosphoranylidene)propionate

(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene

[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane