(5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester

Base Information

• Chemical Name: (5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester
• CAS No.: 218435-13-3
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347
• Mol file: 218435-13-3.mol

Synonyms:(5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester

Chemical Property of (5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester

There total 1 articles about (5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic 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: 52.0%

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1,81114-98-9,67609-52-3) + (2R)-2-[(4-methoxybenzyl)oxy]propanal (218435-12-2) → (5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester (218435-13-3)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -100 ℃; for 0.5h;

DOI:10.1016/S0040-4020(98)00889-8

Reference yield: 82.0%

(5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester (218435-13-3) → (3R,5R,6R)-3,5-Dihydroxy-6-(4-methoxy-benzyloxy)-heptanoic acid methyl ester (218435-14-4)

Guidance literature:

With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -40 ℃; for 24h;

DOI:10.1016/S0040-4020(98)00889-8

Reference yield:

(5R,6R)-5-Hydroxy-6-(4-methoxy-benzyloxy)-3-oxo-heptanoic acid methyl ester (218435-13-3) → (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one (218435-19-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 24 h / -40 °C

2: aq. NaOH / tetrahydrofuran / 0.08 h / Ambient temperature

3: benzene / 15 h / Heating

4: 74 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4020(98)00889-8

upstream raw materials:

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

(2R)-2-[(4-methoxybenzyl)oxy]propanal

Downstream raw materials:

(3R,5R,6R)-3,5-Dihydroxy-6-(4-methoxy-benzyloxy)-heptanoic acid methyl ester

(4R,6R)-4-Hydroxy-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one

2-{(4S,6R)-6-[(R)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanol

{(4R,6R)-6-[(R)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid methyl ester