(2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

Base Information

• Chemical Name: (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester
• CAS No.: 181715-06-0
• Molecular Formula: C₄₈H₆₉NO₉Si
• Molecular Weight: 832.163
• Mol file: 181715-06-0.mol

Synonyms:(2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

Chemical Property of (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

There total 10 articles about (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-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: 85.0%

(S)-2-hydroxy-3-methylbutyric acid benzyl ester (65138-05-8) + (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (181715-13-9) → (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester (181715-06-0)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 25 ℃; for 17h;

DOI:10.1021/jo9608329

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) → (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester (181715-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / DBU / acetonitrile / 17 h / 25 °C

2: 85 percent / EDC, DMAP / CH₂Cl₂ / 17 h / 25 °C

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;

DOI:10.1021/jo9608329

Reference yield:

Octanal (124-13-0) → (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester (181715-06-0)

Guidance literature:

Multi-step reaction with 8 steps

2: 100 percent / pyridine, DMAP / CH₂Cl₂ / 1.17 h / 0 - 25 °C

4: KBH₄ / ethanol / 6.5 h / 0 °C

5: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 1) O₃, 2) PPh₃ / 1) CH₂Cl₂, MeOH, -78 deg C, 3 min, 2) CH₂Cl₂, MeOH, 25 deg C, 15 h

7: 100 percent / NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 16 h / 25 °C

8: 85 percent / EDC, DMAP / CH₂Cl₂ / 17 h / 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; potassium borohydride; 2-methyl-but-2-ene; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo9608329

upstream raw materials:

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

(2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid

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

Octanal

Downstream raw materials:

N-desmethylhapalosin

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