tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate

Base Information

• Chemical Name: tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate
• CAS No.: 442913-42-0
• Molecular Formula: C₁₈H₃₀N₂O₃
• Molecular Weight: 322.448
• Mol file: 442913-42-0.mol

Synonyms:tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate

Chemical Property of tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate

There total 3 articles about tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate 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: 86.0%

tert-butyl (2S,5S)-2-[(1,1-diphenylmethylidene)amino]-5-hydroxy-6-[methyl(phenylmethyl)amino]hexanoate (442913-31-7) → tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate (442913-42-0)

Guidance literature:

With water; citric acid; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1002/hlca.200290026

Reference yield:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate (442913-42-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / 9-anthracenylmethyl-chinchonidinium bromide / 18 h / -60 °C

2: 98 percent / methanol / 13 h / 20 °C

3: 86 percent / citric acid; water / tetrahydrofuran / 0.5 h / 20 °C

With water; citric acid; 9-anthracenylmethyl-chinchonidinium bromide; In tetrahydrofuran; methanol;

DOI:10.1002/hlca.200290026

Reference yield:

tert-butyl (2S)-2-[(1,1-diphenylmethylidene)amino]-4-[(2S)-oxiran-2-yl]butanoate (442913-30-6) → tertbutyl (2S,5S)-2-amino-5-hydroxy-6-(N-methyl-N-phenylmethylamino)hexanoate (442913-42-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / methanol / 13 h / 20 °C

2: 86 percent / citric acid; water / tetrahydrofuran / 0.5 h / 20 °C

With water; citric acid; In tetrahydrofuran; methanol;

DOI:10.1002/hlca.200290026

upstream raw materials:

tert-butyl (2S,5S)-2-[(1,1-diphenylmethylidene)amino]-5-hydroxy-6-[methyl(phenylmethyl)amino]hexanoate

N-(diphenylmethylene)glycine tert-butyl ester

tert-butyl (2S)-2-[(1,1-diphenylmethylidene)amino]-4-[(2S)-oxiran-2-yl]butanoate

Downstream raw materials:

bengamide B

(3S,6S)-6-[((2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-(phenylmethoxy)non-6-enoyl)amino]-2,3,4,5,6,7-hexahydro-1-methyl-7-oxoazepin-3-yl acetate