[1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester

Base Information

• Chemical Name: [1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester
• CAS No.: 669065-41-2
• Molecular Formula: C₃₇H₅₃NO₆SSi
• Molecular Weight: 667.982
• Mol file: 669065-41-2.mol

Synonyms:[1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester

Chemical Property of [1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester

There total 1 articles about [1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-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: 94.0%

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) + (1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate (187324-67-0) → [1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester (669065-41-2)

Guidance literature:

(1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate; With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; at -78 ℃; for 2h;

3-(tert-butyldimethylsilanyloxy)propionaldehyde; In hexane; dichloromethane; at -78 - 20 ℃; for 2h;

DOI:10.1021/ol036284k

Reference yield: 96.0%

t-butyldimethylsiyl triflate (69739-34-0) + [1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester (669065-41-2) → [1(1S,2R),2S,3S]-3,5-bis(tert-butyl-dimethylsilyloxy)-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester (669065-50-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; γ-Irradiation;

DOI:10.1021/ol036284k

Reference yield:

[1(1S,2R),2S,3S]-5-(tert-butyl-dimethylsilyloxy)-3-hydroxy-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester (669065-41-2) → [1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-(2,2,2-trichloroethoxymethyl)amide

Guidance literature:

Multi-step reaction with 13 steps

1.1: 96 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C / γ-Irradiation

2.1: 87 percent / i-PtMgCl / tetrahydrofuran / -20 - 20 °C

3.1: DibalH / tetrahydrofuran; hexane / 3 h / -78 °C

4.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

5.1: 94 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 0 °C

6.1: 88 percent / Ph₃P; I₂; imidazole / CH₂Cl₂ / 0.67 h / 0 °C

7.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

7.2: 73 percent / tetrahydrofuran / 8 h / -78 - -30 °C

8.1: 96 percent / Na₂HPO₄; Na/Hg / methanol / 1.5 h / -20 °C

9.1: KH / tetrahydrofuran / 0.15 h / 0 °C

9.2: 95 percent / tetrahydrofuran / 0.33 h / 20 °C

10.1: 91 percent / HF*pyr / pyridine; tetrahydrofuran / 2 h / 0 - 20 °C

11.1: 91 percent / Et₃N; SO₃*pyr / dimethylsulfoxide / 1.33 h / 20 °C

12.1: BF₃*OEt₂ / CH₂Cl₂ / 39 h / -78 - -50 °C

12.2: 61 percent / t-BuOK / tetrahydrofuran / 2 h

With 1H-imidazole; 2,6-dimethylpyridine; disodium hydrogenphosphate; sodium amalgam; pyridine-SO₃ complex; boron trifluoride diethyl etherate; iodine; isopropylmagnesium chloride; potassium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; 12.1: Parikh-Doering oxidation / 13.1: Yamamoto's allylation / 13.2: Peterson olefination;

DOI:10.1021/ol036284k

upstream raw materials:

3-(tert-butyldimethylsilanyloxy)propionaldehyde

(1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

Downstream raw materials:

[1(1S,2R),2S,3S]-3,5-bis(tert-butyl-dimethylsilyloxy)-2-methylpentanoic acid 2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-propyl ester

(2Z,4R,5R,6S)-6,8-bis(tert-butyl-dimethylsilyloxy)-1-(4-methoxybenzyloxy)-3,5-dimethyloct-2-en-4-ol

(2Z,4R,5S,6S)-6,8-bis(tert-butyl-dimethylsilyloxy)-1-(4-methoxybenzyloxy)-3,5-dimethyl-4-triisopropylsilyloxy-oct-2-ene

[1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide