2H-Pyran-2-acetic acid, 6-[(4R,5S,8E,10R)-10-(benzoyloxy)-10-[(4R)-2,2-dimethyl-1,3-dioxolan -4-yl]-4-hydroxy-5-methyl-2-oxo-8-decenyl]-4-[[(1,1-dimethylethyl)dimeth ylsilyl]oxy]tetrahydro-, ethyl ester, (2R,4R,6S)-

Base Information

• Chemical Name: 2H-Pyran-2-acetic acid, 6-[(4R,5S,8E,10R)-10-(benzoyloxy)-10-[(4R)-2,2-dimethyl-1,3-dioxolan -4-yl]-4-hydroxy-5-methyl-2-oxo-8-decenyl]-4-[[(1,1-dimethylethyl)dimeth ylsilyl]oxy]tetrahydro-, ethyl ester, (2R,4R,6S)-
• CAS No.: 488721-35-3
• Molecular Formula: C38H60O10Si
• Molecular Weight: 704.974
• Mol file: 488721-35-3.mol

Synonyms:

Chemical Property of 2H-Pyran-2-acetic acid, 6-[(4R,5S,8E,10R)-10-(benzoyloxy)-10-[(4R)-2,2-dimethyl-1,3-dioxolan -4-yl]-4-hydroxy-5-methyl-2-oxo-8-decenyl]-4-[[(1,1-dimethylethyl)dimeth ylsilyl]oxy]tetrahydro-, ethyl ester, (2R,4R,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-2-acetic acid, 6-[(4R,5S,8E,10R)-10-(benzoyloxy)-10-[(4R)-2,2-dimethyl-1,3-dioxolan -4-yl]-4-hydroxy-5-methyl-2-oxo-8-decenyl]-4-[[(1,1-dimethylethyl)dimeth ylsilyl]oxy]tetrahydro-, ethyl ester, (2R,4R,6S)-

There total 18 articles about 2H-Pyran-2-acetic acid, 6-[(4R,5S,8E,10R)-10-(benzoyloxy)-10-[(4R)-2,2-dimethyl-1,3-dioxolan -4-yl]-4-hydroxy-5-methyl-2-oxo-8-decenyl]-4-[[(1,1-dimethylethyl)dimeth ylsilyl]oxy]tetrahydro-, ethyl ester, (2R,4R,6S)- 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: 81.0%

Benzoic acid (E)-(1R,6S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-7-oxo-hept-2-enyl ester (488721-34-2) + [(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (488721-30-8) → Benzoic acid (E)-(1R,6S,7R)-10-[(2S,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-ethoxycarbonylmethyl-tetrahydro-pyran-2-yl]-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-6-methyl-9-oxo-dec-2-enyl ester (488721-35-3)

Guidance literature:

[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester; With triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; at 0 ℃; for 3h;

Benzoic acid (E)-(1R,6S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-7-oxo-hept-2-enyl ester; In diethyl ether; at -78 ℃; for 24h;

DOI:10.1021/jo034964v

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (E)-(1R,6S,7R)-10-[(2S,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-ethoxycarbonylmethyl-tetrahydro-pyran-2-yl]-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-6-methyl-9-oxo-dec-2-enyl ester (488721-35-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LiAlH₄ / tetrahydrofuran / 5 h / 20 °C

1.2: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

2.1: 96 percent / TBAF / tetrahydrofuran / 24 h / 0 - 20 °C

3.1: 87 percent / 4 Angstroem molecular sieves; NMO; TPAP / CH₂Cl₂ / 0.17 h / 20 °C

4.1: (-)-B-chloro-diisopinocampheyl borane; Et₃N / diethyl ether / 3 h / 0 °C

4.2: 81 percent / diethyl ether / 24 h / -78 °C

With lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; triethylamine; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 3.1: Ley oxidation;

DOI:10.1021/jo034964v

Reference yield:

[(2R,4S,6S)-4-Hydroxy-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (488721-28-4) → Benzoic acid (E)-(1R,6S,7R)-10-[(2S,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-ethoxycarbonylmethyl-tetrahydro-pyran-2-yl]-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-6-methyl-9-oxo-dec-2-enyl ester (488721-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: imidazole; DMAP / dimethylformamide / 20 h / 20 °C

2.1: 86 percent / PdCl₂; CuCl; air / dimethylformamide; H₂O / 48 h / 20 °C

3.1: (-)-B-chloro-diisopinocampheyl borane; Et₃N / diethyl ether / 3 h / 0 °C

3.2: 81 percent / diethyl ether / 24 h / -78 °C

With 1H-imidazole; dmap; air; triethylamine; (-)-diisopinocamphenylborane chloride; copper(l) chloride; palladium dichloride; In diethyl ether; water; N,N-dimethyl-formamide; 2.1: Wacker oxidation;

DOI:10.1021/jo034964v

upstream raw materials:

Benzoic acid (E)-(1R,6S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-7-oxo-hept-2-enyl ester

[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

benzoyl chloride

6-((E)-(S)-2-Hydroxy-pent-3-enyl)-2,2-dimethyl-[1,3]dioxin-4-one

Downstream raw materials:

[4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-1-(2,4,6-triisopropyl-phenylselanyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-hydroxy-propyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Benzoic acid (E)-(1R,6S,7R,9R)-10-[(2R,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-ethoxycarbonylmethyl-tetrahydro-pyran-2-yl]-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7,9-dihydroxy-6-methyl-dec-2-enyl ester