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

Base Information

• Chemical Name: (4R,6R)-4-Hydroxy-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one
• CAS No.: 218435-18-8
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 218435-18-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (4R,6R)-4-Hydroxy-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one 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:

(3R,5R,6R)-3,5-Dihydroxy-6-(4-methoxy-benzyloxy)-heptanoic acid methyl ester (218435-14-4) → (4R,6R)-4-Hydroxy-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one (218435-18-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2: benzene / 15 h / Heating

With sodium hydroxide; In tetrahydrofuran; benzene;

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-Hydroxy-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one (218435-18-8)

Guidance literature:

Multi-step reaction with 3 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

With sodium hydroxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; acetic acid; acetonitrile; benzene;

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

Reference yield:

(2R)-2-[(4-methoxybenzyl)oxy]propanal (218435-12-2) → (4R,6R)-4-Hydroxy-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one (218435-18-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / SnCl₄ / CH₂Cl₂ / 0.5 h / -100 °C

2: 82 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 24 h / -40 °C

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

4: benzene / 15 h / Heating

With sodium hydroxide; tin(IV) chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetic acid; acetonitrile; benzene;

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

upstream raw materials:

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

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

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

Downstream raw materials:

(4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(R)-1-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-one

(3R,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-(2-trimethylsilanyl-ethoxymethoxy)-heptanal

1-[(E)-(1R,2R,4S)-7-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-hept-6-enyloxymethyl]-4-methoxy-benzene

(3R,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-(2-trimethylsilanyl-ethoxymethoxy)-heptanoic acid methoxy-methyl-amide