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

Base Information

• Chemical Name: tert-butyl (2R,3R)-1-(4-tert-butoxyphenyl)-3-hydroxyhept-6-en-2-yl(methyl)carbamate
• CAS No.: 1246843-15-1
• Molecular Formula: C₂₃H₃₇NO₄
• Molecular Weight: 391.551
• Mol file: 1246843-15-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about tert-butyl (2R,3R)-1-(4-tert-butoxyphenyl)-3-hydroxyhept-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 1-(4-tert-butoxyphenyl)-3-oxohept-6-en-2-yl(methyl)carbamate (1246843-14-0) → tert-butyl (2R,3R)-1-(4-tert-butoxyphenyl)-3-hydroxyhept-6-en-2-yl(methyl)carbamate (1246843-15-1)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol101801u

Reference yield:

C19H29NO4 + 4-but-1-enylmagnesium bromide (7103-09-5) → tert-butyl (2R,3R)-1-(4-tert-butoxyphenyl)-3-hydroxyhept-6-en-2-yl(methyl)carbamate (1246843-15-1) + C23H37NO4 (1292308-92-9)

Guidance literature:

C₁₉H₂₉NO₄; 4-but-1-enylmagnesium bromide; In tetrahydrofuran; at -78 - -5 ℃; for 4.5h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; at -10 ℃; optical yield given as %de; Saturated solution;

DOI:10.1016/j.bmc.2011.01.027

Reference yield:

(R)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-tert-butoxyphenyl)propanoic acid (1246843-12-8) → tert-butyl (2R,3R)-1-(4-tert-butoxyphenyl)-3-hydroxyhept-6-en-2-yl(methyl)carbamate (1246843-15-1)

Guidance literature:

Multi-step reaction with 3 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

3: L-Selectride / tetrahydrofuran / -78 °C / Inert atmosphere

With L-Selectride; 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

upstream raw materials:

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

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

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

4-but-1-enylmagnesium bromide

Downstream raw materials:

C₁₉H₂₇NO₃

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

C₄₅H₆₇NO₅Si