(S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate

Base Information

• Chemical Name: (S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate
• CAS No.: 173204-70-1
• Molecular Formula: C₂₄H₃₈O₆
• Molecular Weight: 422.562
• Mol file: 173204-70-1.mol

Synonyms:(S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate

Chemical Property of (S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate

There total 10 articles about (S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate 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: 46.0%

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + (2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-decanoyl chloride (1026690-76-5) → (S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate (173204-70-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00130a001

Reference yield:

(2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoic acid (173204-73-4) → (S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate (173204-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂, i-Pr₂NEt / CH₂Cl₂ / 2 h / 0 °C

2: i-Pr₂NEt / CH₂Cl₂ / 25 °C

With thionyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo9608329

Reference yield:

Octanal (124-13-0) → (S)-1-carboxy-2-methylpropyl (2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoate (173204-70-1)

Guidance literature:

Multi-step reaction with 6 steps

2: 80 percent / TfOH / tetrahydrofuran / 5 h / 25 °C

3: 1) O₃, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C, 8 min, 2) CH₂Cl₂, 25 deg C, overnight

4: 100 percent / NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 25 °C

5: SOCl₂, i-Pr₂NEt / CH₂Cl₂ / 2 h / 0 °C

6: i-Pr₂NEt / CH₂Cl₂ / 25 °C

With sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; trifluorormethanesulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo9608329

upstream raw materials:

(S)-2-Hydroxy-3-methylbutanoic acid

(2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-decanoyl chloride

Octanal

(2S,3R)-3-p-<(methoxybenzyl)oxy>-2-methyldecanoic acid

Downstream raw materials:

(-)-hapalosin

(2S,3R)-3-Hydroxy-2-methyl-decanoic acid (S)-1-{[(1S,2R)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamoyl}-2-methyl-propyl ester

(2S,3R)-3-Hydroxy-2-methyl-decanoic acid (S)-1-{[(1S,2R)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl]-methyl-carbamoyl}-2-methyl-propyl ester

(2S,3R)-3-Hydroxy-2-methyl-decanoic acid (S)-1-{[(1S,2R)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-3-carboxy-propyl]-methyl-carbamoyl}-2-methyl-propyl ester