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

Base Information

• Chemical Name: (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-(tert-butyldimethylsilyloxy)-2-methyldecanoate
• CAS No.: 182621-40-5
• Molecular Formula: C₂₉H₅₀O₅Si
• Molecular Weight: 506.798
• Mol file: 182621-40-5.mol

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

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

There total 11 articles about (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-(tert-butyldimethylsilyloxy)-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: 90.0%

(S)-2-hydroxy-3-methylbutyric acid benzyl ester (65138-05-8) + (2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methyl-decanoic acid (182621-38-1) → (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-(tert-butyldimethylsilyloxy)-2-methyldecanoate (182621-40-5)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 0 - 25 ℃; for 8h;

DOI:10.1055/s-0033-1338952

Reference yield:

Octanal (124-13-0) → (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-(tert-butyldimethylsilyloxy)-2-methyldecanoate (182621-40-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 - 0 °C

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

3: 98 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O / Ambient temperature

4: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1.) THF, rt, 30 min, 2.) THF, TolH, rt, 18 h

With 2,6-dimethylpyridine; dmap; lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; dihydrogen peroxide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0968-0896(98)00208-9

Reference yield:

(4S)-3<(2'S,3'R)-2'-methyl-3'-hydroxydecanoyl>-4-phenylmethyl-2-oxazolidinone (182621-36-9) → (2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-(tert-butyldimethylsilyloxy)-2-methyldecanoate (182621-40-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2: 98 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O / Ambient temperature

3: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) DMAP / 1.) THF, rt, 30 min, 2.) THF, TolH, rt, 18 h

With 2,6-dimethylpyridine; dmap; lithium hydroxide; 2,4,6-trichlorobenzoyl chloride; dihydrogen peroxide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0968-0896(98)00208-9

upstream raw materials:

(S)-2-hydroxy-3-methylbutyric acid benzyl ester

(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methyl-decanoic acid

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

benzyl bromide

Downstream raw materials:

(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

(2S,5S,6S,10R,11S)-5-Benzyl-10-heptyl-2-isopropyl-6-methoxymethoxy-4,11-dimethyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione

(2S,5S,6S,10R,11S)-5-Benzyl-10-heptyl-6-hydroxy-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione