(2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol

Base Information

• Chemical Name: (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol
• CAS No.: 173204-72-3
• Molecular Formula: C₁₈H₂₇NO₃
• Molecular Weight: 305.417
• Mol file: 173204-72-3.mol

Synonyms:(2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol

Chemical Property of (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol

There total 7 articles about (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol 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: 88.0%

Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (238753-81-6) → (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol (173204-72-3)

Guidance literature:

In tetrahydrofuran; at -30 ℃; for 6h;

DOI:10.1055/s-1999-2765

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol (173204-72-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / NaH / dimethylformamide / 15 h / 25 °C

2: 72 percent / DIBAH / toluene; various solvent(s) / 2.5 h / -78 °C

With sodium hydride; diisobutylaluminium hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9608329

Reference yield:

(S)-methyl 2-((tert-butoxycarbonyl)(methyl)amino)-3-phenylpropanoate (37553-64-3) → (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol (173204-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / DIBAH / toluene; various solvent(s) / 2.5 h / -78 °C

With diisobutylaluminium hydride; In toluene;

DOI:10.1021/jo9608329

upstream raw materials:

tert-butyl (S)-N-methyl-N-(1-oxo-3-phenylpropan-2-yl)carbamate

allylmagnesium bromide

Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

(2S,3R)-2-Methylamino-1-phenyl-hex-5-en-3-ol

((1S,2R)-1-Benzyl-2-methoxymethoxy-pent-4-enyl)-methyl-carbamic acid tert-butyl ester

[1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester

(2S,5S,6R,10R,11S)-5-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10-heptyl-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione