(2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid

Base Information

• Chemical Name: (2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid
• CAS No.: 400009-40-7
• Molecular Formula: C₂₀H₂₆N₂O₇
• Molecular Weight: 406.436
• Mol file: 400009-40-7.mol

Synonyms:(2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid

Chemical Property of (2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid

There total 9 articles about (2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid 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: 90.0%

(1S,2'R,4'RS)-1-(1'-benzyloxycarbonyl-4'-hydroxypiperidin-2'-yl)-2-hydroxyethylcarbamic acid tert-butyl ester → (2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid (400009-40-7)

Guidance literature:

With jones reagent; In acetone; at 0 - 25 ℃; for 6h;

DOI:10.1021/jo016186h

Reference yield: 83.0%

(1S,2'R)-1-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-2-(hydroxy)ethylcarbamic acid tert-butyl ester (629648-09-5) → (2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid (400009-40-7)

Guidance literature:

With jones reagent; In acetone; at 0 - 20 ℃; for 5h;

DOI:10.1016/j.tet.2003.08.060

Reference yield:

tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate (124085-68-3) → (2S,2'R)-tert-butoxycarbonylamino-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-acetic acid (400009-40-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / CHCl₃ / 30 h / 25 °C

2.1: tetrahydrofuran / 120 h / 0 °C

2.2: H₂; Pd(OH)2 / methanol / 20 h / 25 °C / 2585.74 Torr

2.3: 0.20 g / Na₂CO₃*10H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

3.1: 94 percent / Bu₄NF / tetrahydrofuran / 20 °C

4.1: 83 percent / Jones reagent / acetone / 5 h / 0 - 20 °C

With jones reagent; tetrabutyl ammonium fluoride; In tetrahydrofuran; chloroform; acetone; 1.1: Wittig reaction / 2.1: Michael reaction;

DOI:10.1016/j.tet.2003.08.060

upstream raw materials:

(1S,2'R)-1-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-2-(hydroxy)ethylcarbamic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate

benzylamine

Downstream raw materials:

(2S,2'R)-tert-butoxycarbonylamino-(4'-oxopiperidin-2'-yl)-acetic acid