(2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate

Base Information

• Chemical Name: (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate
• CAS No.: 182621-41-6
• Molecular Formula: C₂₃H₃₆O₅
• Molecular Weight: 392.536
• Mol file: 182621-41-6.mol

Synonyms:(2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate

Chemical Property of (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate

There total 21 articles about (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-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: 93.0%

(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl (2S,3R)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)decanoate (174623-93-9) → (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate (182621-41-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00772-9

Reference yield: 90.0%

(2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-(tert-butyldimethylsilyloxy)-2-methyldecanoate (182621-40-5) → (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate (182621-41-6)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1016/0040-4039(96)01415-3

Reference yield:

(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methyl-decanoic acid (182621-38-1) → (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate (182621-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: EDC, DMAP / CH₂Cl₂ / 0 - 20 °C

2: HF, pyridine / acetonitrile / 0 °C

With pyridine; dmap; hydrogen fluoride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; acetonitrile;

DOI:10.1016/S0960-894X(99)00243-7

upstream raw materials:

(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl (2S,3R)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)decanoate

(2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-(tert-butyldimethylsilyloxy)-2-methyldecanoate

Octanal

(2S,3R)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)decanoic acid

Downstream raw materials:

(2S,3R)-(R)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl-3-{[(3R,4S)-4-{[(benzyloxy)carbonyl](methyl)amino}-3-(methoxymethoxy)-5-phenylpentanoyl]oxy}-2-methyldecanoate

(2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

(2S,3S)-3-[(E)-(S)-4-(Benzyloxycarbonyl-methyl-amino)-5-phenyl-pent-2-enoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

(1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-3-O-(methoxymethyl)-5-phenyl-L-erythro-pentonate