methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate

Base Information

• Chemical Name: methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate
• CAS No.: 865178-80-9
• Molecular Formula: C₁₆H₂₁NO₇S
• Molecular Weight: 371.411
• Mol file: 865178-80-9.mol

Synonyms:methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate

Chemical Property of methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate

There total 1 articles about methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate 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: 70.0%

methanesulfonyl chloride (124-63-0) + cis-5(S)-hydroxy-2(S)-N1-benzyloxycarbonylpipecolic acid methyl ester (117836-26-7) → methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate (865178-80-9)

Guidance literature:

With pyridine; for 2h; cooling;

DOI:10.1021/jo0506884

Reference yield: 90.0%

methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate (865178-80-9) → methyl (2S,5R)-5-azido-N-(benzyloxycarbonyl)pipecolate (865178-81-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 12h;

DOI:10.1021/jo0506884

Reference yield:

methyl (2S,5S)-5-O-methylsulfonyl-N-(benzyloxycarbonyl)pipecolate (865178-80-9) → methyl (2S,5R)-5-(tert-butoxycarbonylamino)-1-N-(benzyloxycarbonyl)pipecolate (865178-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaN₃ / dimethylformamide / 12 h / 60 °C

2: 90 percent / hydrogen / Ra/Ni / ethyl acetate / 2 h / 2068.59 Torr

With sodium azide; hydrogen; nickel; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo0506884

upstream raw materials:

methanesulfonyl chloride

cis-5(S)-hydroxy-2(S)-N₁-benzyloxycarbonylpipecolic acid methyl ester

Downstream raw materials:

methyl (2S,5R)-5-azido-N-(benzyloxycarbonyl)pipecolate

methyl (2S,5R)-5-(tert-butoxycarbonylamino)-1-N-(benzyloxycarbonyl)pipecolate

(2S,5R)-5-(tert-butoxycarbonylamino)-1-N-(thyminylacetyl)pipecolic acid

methyl (2S,5R)-5-(tert-butoxycarbonylamino)-1-N-(thyminylacetyl)pipecolate