2H-Pyran-2-one, 6-[(1S,2R,5R,7S)-8-azido-2-(benzoyloxy)-1-[(4-methoxyphenyl)methoxy ]-5,7-dimethyl-4-oxooctyl]tetrahydro-4-methyl-, (4R,6S)-

Base Information

• Chemical Name: 2H-Pyran-2-one, 6-[(1S,2R,5R,7S)-8-azido-2-(benzoyloxy)-1-[(4-methoxyphenyl)methoxy ]-5,7-dimethyl-4-oxooctyl]tetrahydro-4-methyl-, (4R,6S)-
• CAS No.: 343783-01-7
• Molecular Formula: C31H39N3O7
• Molecular Weight: 565.667
• Mol file: 343783-01-7.mol

Synonyms:

Chemical Property of 2H-Pyran-2-one, 6-[(1S,2R,5R,7S)-8-azido-2-(benzoyloxy)-1-[(4-methoxyphenyl)methoxy ]-5,7-dimethyl-4-oxooctyl]tetrahydro-4-methyl-, (4R,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-2-one, 6-[(1S,2R,5R,7S)-8-azido-2-(benzoyloxy)-1-[(4-methoxyphenyl)methoxy ]-5,7-dimethyl-4-oxooctyl]tetrahydro-4-methyl-, (4R,6S)-

There total 21 articles about 2H-Pyran-2-one, 6-[(1S,2R,5R,7S)-8-azido-2-(benzoyloxy)-1-[(4-methoxyphenyl)methoxy ]-5,7-dimethyl-4-oxooctyl]tetrahydro-4-methyl-, (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: 96.0%

benzoyl chloride (98-88-4) + (4R,6S)-6-[(1R,2R,5R,7S)-8-Azido-2-hydroxy-1-(4-methoxy-benzyloxy)-5,7-dimethyl-4-oxo-octyl]-4-methyl-tetrahydro-pyran-2-one (343782-90-1) → Benzoic acid (1R,4R,6S)-7-azido-1-[(S)-(4-methoxy-benzyloxy)-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-methyl]-4,6-dimethyl-3-oxo-heptyl ester (343783-01-7)

Guidance literature:

With pyridine; at 0 ℃; for 2h;

DOI:10.1002/1521-3773(20010401)40:7<1262::AID-ANIE1262>3.0.CO;2-9

Reference yield:

(3R,5S)-3,5-dimethyltetrahydro-2H-pyran-2-one (74034-73-4,3290-57-1) → Benzoic acid (1R,4R,6S)-7-azido-1-[(S)-(4-methoxy-benzyloxy)-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-methyl]-4,6-dimethyl-3-oxo-heptyl ester (343783-01-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / AlMe₃ / tetrahydrofuran; toluene / 4 h / 0 °C

2.1: 96 percent / Et₃N / CH₂Cl₂ / 18 h / 25 °C

3.1: 96 percent / NaN₃ / dimethylformamide / 96 h / 25 °C

4.1: 82 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C

5.1: chlorodicyclohexylborane; N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 0 °C

5.2: CH₂Cl₂ / 3.5 h / -78 °C

5.3: 93 percent / aq. H₂O₂ / methanol; various solvent(s) / 12 h / -78 - 25 °C / pH 7

6.1: 88 percent / pyridine / 4 h / 0 °C

With pyridine; sodium azide; dicyclohexylboron chloride; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0547477

Reference yield:

(2R,4S)-5-Azido-2,4-dimethyl-pentanoic acid methoxy-methyl-amide (343782-85-4) → Benzoic acid (1R,4R,6S)-7-azido-1-[(S)-(4-methoxy-benzyloxy)-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-methyl]-4,6-dimethyl-3-oxo-heptyl ester (343783-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C

2.1: chlorodicyclohexylborane; N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 0 °C

2.2: CH₂Cl₂ / 3.5 h / -78 °C

2.3: 93 percent / aq. H₂O₂ / methanol; various solvent(s) / 12 h / -78 - 25 °C / pH 7

3.1: 88 percent / pyridine / 4 h / 0 °C

With pyridine; dicyclohexylboron chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja0547477

upstream raw materials:

benzoyl chloride

(4R,6S)-6-[(1R,2R,5R,7S)-8-Azido-2-hydroxy-1-(4-methoxy-benzyloxy)-5,7-dimethyl-4-oxo-octyl]-4-methyl-tetrahydro-pyran-2-one

(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)propanal

[(4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-yl]-methanol

Downstream raw materials:

Benzoic acid (1R,4R,6S)-7-azido-1-[(S)-hydroxy-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-methyl]-4,6-dimethyl-3-oxo-heptyl ester