(R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate

Base Information

• Chemical Name: (R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate
• CAS No.: 1246843-14-0
• Molecular Formula: C₂₃H₃₅NO₄
• Molecular Weight: 389.535
• Mol file: 1246843-14-0.mol

Synonyms:(R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate

Chemical Property of (R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate

There total 3 articles about (R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate 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: 89.0%

(R)-tert-butyl 3-(4-tert-butoxyphenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl(methyl)carbamate (1246843-13-9) + 4-but-1-enylmagnesium bromide (7103-09-5) → (R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate (1246843-14-0)

Guidance literature:

(R)-tert-butyl 3-(4-tert-butoxyphenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl(methyl)carbamate; 4-but-1-enylmagnesium bromide; In tetrahydrofuran; at -15 - 0 ℃; for 4h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/ol101801u

Reference yield:

(R)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-tert-butoxyphenyl)propanoic acid (1246843-12-8) → (R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate (1246843-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / Inert atmosphere

2: tetrahydrofuran / Inert atmosphere

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2011.01.027

Reference yield:

Boc-D-Tyr(t-Bu)-OH (507276-74-6) → (R)-tert-butyl 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate (1246843-14-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / Inert atmosphere

3: tetrahydrofuran / Inert atmosphere

With sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.01.027

upstream raw materials:

(R)-tert-butyl 3-(4-tert-butoxyphenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl(methyl)carbamate

4-but-1-enylmagnesium bromide

(R)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-tert-butoxyphenyl)propanoic acid

Boc-D-Tyr(t-Bu)-OH

Downstream raw materials:

tert-butyl (2R,3R)-1-(4-tert-butoxyphenyl)-3-hydroxyhept-6-en-2-yl(methyl)carbamate

(2R,3R)-2-(tert-butoxycarbonyl(methyl)amino)-1-(4-tert-butoxyphenyl)hept-6-en-3-yl acetate

C₃₀H₄₉NO₅

C₂₈H₄₇NO₄