(2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 408505-24-8
• Molecular Formula: C₃₈H₅₀N₂O₄S
• Molecular Weight: 630.892
• Mol file: 408505-24-8.mol

Synonyms:(2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 17 articles about (2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl 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:

tert-butyl (2R,3S)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-3-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate (408505-23-7) → (2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (408505-24-8)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1016/S0957-4166(03)00597-4

Reference yield:

(2E)-2-methyl-2-penten-1-ol (16958-19-3) → (2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (408505-24-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: (-)-dimethyl D-tartrate; titanium tetraisopropoxide; tert-butylhydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 4 h / -20 °C

2.1: 7.35 g / trimethylphosphite; triethylamine / CH₂Cl₂; decane / 1.5 h

3.1: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C

4.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C

5.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C

6.1: hydrogen / 20percent Pd(OH)2 on carbon / CH₂Cl₂ / 3.5 h

7.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 1.5 h / 20 °C

8.1: pyridinium p-toluenesulfonate; MgSO₄ / diethyl ether / 18 h / 20 °C

9.1: 52 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 - -50 °C

10.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

10.2: CuBr*Me₂S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C

10.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C

11.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; Dimethyl D-tartrate; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; magnesium sulfate; magnesium; ethylene dibromide; triethylamine; pyridinium chlorochromate; phosphorous acid trimethyl ester; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; decane; hexane; dichloromethane; 10.3: Michael addition;

DOI:10.1021/jo0162890

Reference yield:

methyl (2E)-2-methyl-2-pentenoate (1567-14-2) → (2R,3S)-5-Hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (408505-24-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 80 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 - 20 °C

2.1: (-)-dimethyl D-tartrate; titanium tetraisopropoxide; tert-butylhydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 4 h / -20 °C

3.1: 7.35 g / trimethylphosphite; triethylamine / CH₂Cl₂; decane / 1.5 h

4.1: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C

5.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C

6.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C

7.1: hydrogen / 20percent Pd(OH)2 on carbon / CH₂Cl₂ / 3.5 h

8.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 1.5 h / 20 °C

9.1: pyridinium p-toluenesulfonate; MgSO₄ / diethyl ether / 18 h / 20 °C

10.1: 52 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 - -50 °C

11.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

11.2: CuBr*Me₂S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C

11.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C

12.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; Dimethyl D-tartrate; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; magnesium sulfate; magnesium; ethylene dibromide; triethylamine; pyridinium chlorochromate; phosphorous acid trimethyl ester; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; decane; hexane; dichloromethane; 11.3: Michael addition;

DOI:10.1021/jo0162890

upstream raw materials:

tert-butyl (2R,3S)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-3-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate

(+/-)-2-methoxy-2-methyl-pentanoic acid

N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole

(2S)-2-methoxy-2-methyl-pentylidene-N-triphenylmethylsulfenamide

Downstream raw materials:

tert-butyl (2R,3S,5R)-5-cyano-2-{(1R,2S)-2-methoxy-2-methyl-1-[(tritylthio)amino]pentyl}-3-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate

A-315675

(2R,3S)-5-Methoxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester