(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

Base Information

• Chemical Name: (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
• CAS No.: 173204-68-7
• Molecular Formula: C₃₄H₅₉NO₇Si
• Molecular Weight: 621.93
• Mol file: 173204-68-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 21 articles about (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 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:

(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 (173204-78-9) → (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 (173204-68-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene;

DOI:10.1021/jo00130a001

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) → (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 (173204-68-7)

Guidance literature:

Multi-step reaction with 7 steps

1: i-Pr₂NEt / CH₂Cl₂ / 25 °C

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

3: i-Pr₂NEt / CH₂Cl₂ / 1.5 h

4: 89 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

5: 85 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 25 °C

6: 1) O₃, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, 25 deg C, overnight

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

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo9608329

Reference yield:

(2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-decanoyl chloride (1026690-76-5) → (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 (173204-68-7)

Guidance literature:

Multi-step reaction with 7 steps

1: i-Pr₂NEt / CH₂Cl₂ / 25 °C

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

3: i-Pr₂NEt / CH₂Cl₂ / 1.5 h

4: 89 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

5: 85 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 25 °C

6: 1) O₃, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, 25 deg C, overnight

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

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo9608329

upstream raw materials:

(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

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

Octanal

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Downstream raw materials:

(-)-hapalosin

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