(2R,3R)-[((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl)-3-tertbutyldimethylsilyloxy]-2-methylpentanoate

Base Information

• Chemical Name: (2R,3R)-[((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl)-3-tertbutyldimethylsilyloxy]-2-methylpentanoate
• CAS No.: 1361332-19-5
• Molecular Formula: C₃₇H₅₃NO₅SSi
• Molecular Weight: 651.983
• Mol file: 1361332-19-5.mol

Synonyms:(2R,3R)-[((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl)-3-tertbutyldimethylsilyloxy]-2-methylpentanoate

Chemical Property of (2R,3R)-[((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl)-3-tertbutyldimethylsilyloxy]-2-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-[((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl)-3-tertbutyldimethylsilyloxy]-2-methylpentanoate

There total 1 articles about (2R,3R)-[((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl)-3-tertbutyldimethylsilyloxy]-2-methylpentanoate 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: 100.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,3R)-(1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl-3-hydroxy-2-methylpentanoate → (2R,3R)-[((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl)-3-tertbutyldimethylsilyloxy]-2-methylpentanoate (1361332-19-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1002/anie.201106435

Reference yield:

(2R,3R)-[((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl)-3-tertbutyldimethylsilyloxy]-2-methylpentanoate (1361332-19-5) → C47H70N2O10Si2

Guidance literature:

Multi-step reaction with 13 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2.33 h / -40 °C

3.2: 1.5 h / -78 °C

4.1: 2,6-dimethylpyridine / dichloromethane / -78 - 20 °C

5.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0 - 20 °C

6.1: benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

6.2: 20 °C

7.1: diethylamino-sulfur trifluoride / dichloromethane / 3 h / -78 °C

7.2: -78 - 20 °C

8.1: hexamethylenetetramine; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(ll) bromide / dichloromethane / 6 h / 20 °C

9.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

9.2: 20 °C

10.1: potassium carbonate / methanol / 0 - 20 °C

11.1: Schwartz's reagent / tetrahydrofuran / 1 h / 0 °C

11.2: 0.42 h / -78 °C / Darkness

12.1: n-butyllithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere

12.2: 0.25 h / -78 °C

12.3: 3 h / -78 °C

13.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 39 h / 0 - 20 °C

With 2,6-dimethylpyridine; Schwartz's reagent; n-butyllithium; diethylamino-sulfur trifluoride; hexamethylenetetramine; dihydrogen peroxide; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(ll) bromide; lithium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; pentane; 3.1: Nagao reaction / 3.2: Nagao reaction;

DOI:10.1002/anie.201106435

upstream raw materials:

t-butyldimethylsiyl triflate