tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate

Base Information

• Chemical Name: tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate
• CAS No.: 860781-14-2
• Molecular Formula: C₂₁H₃₁NO₇S
• Molecular Weight: 442.538
• Mol file: 860781-14-2.mol

Synonyms:tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate

Chemical Property of tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate

There total 7 articles about tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate 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: 71.0%

tert-butyl (2S,3S,4S)-[3-2H1]-N-tert-butoxycarbonyl-4-hydroxyprolinate (860781-11-9) + p-toluenesulfonyl chloride (98-59-9) → tert-butyl (2S,3S,4S)-[3-2H1]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate (860781-14-2)

Guidance literature:

With pyridine; at 20 ℃; for 20h;

DOI:10.1016/j.tetlet.2005.04.126 DOI:10.1039/b601097k

Reference yield:

tert-butyl (2S)-[3,3-2H2]-N-tert-butoxycarbonyl-4-oxoprolinate (860781-19-7) → tert-butyl (2S,3S,4S)-[3-2H1]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate (860781-14-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: 3.9 g / aq. NH₄Cl / tetrahydrofuran; hexane / 20 °C

3.1: 40 percent / NaBH₄ / methanol; diethyl ether / 0.58 h / 0 - 20 °C

4.1: 71 percent / pyridine / 20 h / 20 °C

With pyridine; sodium tetrahydroborate; ammonium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane;

DOI:10.1039/b601097k

Reference yield:

C17H30(2)HNO5Si → tert-butyl (2S,3S,4S)-[3-2H1]-N-tert-butoxycarbonyl-4-O-para-toluenesulfonyloxyprolinate (860781-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.9 g / aq. NH₄Cl / tetrahydrofuran; hexane / 20 °C

2: 40 percent / NaBH₄ / methanol; diethyl ether / 0.58 h / 0 - 20 °C

3: 71 percent / pyridine / 20 h / 20 °C

With pyridine; sodium tetrahydroborate; ammonium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane;

DOI:10.1039/b601097k

upstream raw materials:

tert-butyl (2S,3S,4S)-[3-²H₁]-N-tert-butoxycarbonyl-4-hydroxyprolinate

p-toluenesulfonyl chloride

tert-butyl (2S,3S)-[3-²H₁]-N-tert-butoxycarbonyl-4-oxoprolinate

tert-butyl (2S)-[3,3-²H₂]-N-tert-butoxycarbonyl-4-oxoprolinate