6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester

Base Information

• Chemical Name: 6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester
• CAS No.: 467234-69-1
• Molecular Formula: C₄₉H₇₇ClNO₁₃PSi
• Molecular Weight: 982.662
• Mol file: 467234-69-1.mol

Synonyms:6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester

Chemical Property of 6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester

There total 9 articles about 6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl 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: 87.0%

diallyl diisopropylphosphoramidite (126429-21-8) + (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-5-(2-chloro-acetoxy)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-7-hydroxy-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester (467234-68-0) → 6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester (467234-69-1)

Guidance literature:

diallyl diisopropylphosphoramidite; (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-5-(2-chloro-acetoxy)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-7-hydroxy-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester; With 1H-tetrazole; In dichloromethane; acetonitrile; at 20 ℃; for 1h;

With tert.-butylhydroperoxide; In ethanol; dichloromethane; acetonitrile; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00528-8

Reference yield:

leustroducsin-H → 6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester (467234-69-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 69 percent / NaHCO₃ / H₂O; dioxane / 2 h / 20 °C

2.1: 72 percent / alkaline phosphatase type-I / various solvent(s) / 48 h / 20 °C / pH 9.3 / Enzymatic reaction

3.1: 56 percent / molecular sieves 5 Angstroem; pyridinium p-toluenesulfonate / CH₂Cl₂ / 16 h / 20 °C

4.1: 90 percent / ethyldiisopropylamine; 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran; CH₂Cl₂ / 1 h / 20 °C

5.1: 85 percent / 50 percent aq. trifluoroacetic acid / tetrahydrofuran / 1 h / 20 °C

6.1: imidazole / CH₂Cl₂ / 12 h / 20 °C

7.1: HF*Py / tetrahydrofuran / 1 h / 0 °C

8.1: 31 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

9.1: 1H-tetrazole / CH₂Cl₂; acetonitrile / 1 h / 20 °C

9.2: 87 percent / t-BuOOH / ethanol; CH₂Cl₂; acetonitrile / 1 h / 0 °C

With pyridine; 1H-imidazole; 1H-tetrazole; dmap; 5A molecular sieve; alkaline phosphatase type-I; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(02)00528-8

Reference yield:

((E)-(R)-5-((2S,3S)-3-Ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-3-hydroxy-3-{(4R,6R)-6-[(1Z,3Z)-4-((1R,3S)-3-hydroxy-cyclohexyl)-buta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-4-enyl)-carbamic acid allyl ester (467234-64-6) → 6-methyl-octanoic acid 3-[8-(2-allyloxycarbonylamino-ethyl)-7-(bis-allyloxy-phosphoryloxy)-5-chloroacetoxy-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester (467234-69-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / ethyldiisopropylamine; 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran; CH₂Cl₂ / 1 h / 20 °C

2.1: 85 percent / 50 percent aq. trifluoroacetic acid / tetrahydrofuran / 1 h / 20 °C

3.1: imidazole / CH₂Cl₂ / 12 h / 20 °C

4.1: HF*Py / tetrahydrofuran / 1 h / 0 °C

5.1: 31 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

6.1: 1H-tetrazole / CH₂Cl₂; acetonitrile / 1 h / 20 °C

6.2: 87 percent / t-BuOOH / ethanol; CH₂Cl₂; acetonitrile / 1 h / 0 °C

With pyridine; 1H-imidazole; 1H-tetrazole; dmap; 2,4,6-trichlorobenzoyl chloride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(02)00528-8

upstream raw materials:

diallyl diisopropylphosphoramidite

(S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-5-(2-chloro-acetoxy)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-7-hydroxy-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester

((E)-(R)-5-((2S,3S)-3-Ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-3-hydroxy-3-{(4R,6R)-6-[(1Z,3Z)-4-((1R,3S)-3-hydroxy-cyclohexyl)-buta-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-4-enyl)-carbamic acid allyl ester

[(7Z,9Z)-(3R,4R,6R)-3-[(E)-2-((2S,3S)-3-Ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-3,4,6-trihydroxy-10-((1R,3S)-3-hydroxy-cyclohexyl)-deca-7,9-dienyl]-carbamic acid allyl ester

Downstream raw materials:

(1S,3R)-3-{(1Z,3Z,5R,7R,8R,9E)-8-(2-{[(allyloxyl)carbonyl]amino}ethyl)-7-{[bis(allyloxy)phosphoryl]oxy}-10-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-5-hydroxy-8-[(trimethylsilyl)oxy]deca-1,3,9-trienyl}cyclohexyl (6S)-6-methyloctanoate

leustroducsin B

Refernces