(2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid

Base Information

• Chemical Name: (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid
• CAS No.: 175656-28-7
• Molecular Formula: C₂₈H₄₁NO₅Si
• Molecular Weight: 499.723
• Mol file: 175656-28-7.mol

Synonyms:(2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid

Chemical Property of (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid

There total 4 articles about (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic 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:

tert-Butyl-((3R,4S)-4-ethyl-3-isocyanato-hex-5-ynyloxy)-diphenyl-silane → (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid (175656-28-7)

Guidance literature:

Multi-step reaction with 2 steps

1: TMSCl / CH₂Cl₂ / 96 h / Ambient temperature

2: 1.) NaHCO₃, KMnO₄, NaIO₄, 2.) KOH / 1.) t-BuOH, H₂O, rt, 3 h, 2.) THF, H₂O, rt, 2.5 h

With potassium hydroxide; potassium permanganate; sodium periodate; chloro-trimethyl-silane; sodium hydrogencarbonate; In dichloromethane;

DOI:10.1021/jo952092u

Reference yield:

(2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-pent-4-ynoic acid (175656-26-5) → (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid (175656-28-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DPPA, Et₃N / benzene / 3.5 h / Heating

2: TMSCl / CH₂Cl₂ / 96 h / Ambient temperature

3: 1.) NaHCO₃, KMnO₄, NaIO₄, 2.) KOH / 1.) t-BuOH, H₂O, rt, 3 h, 2.) THF, H₂O, rt, 2.5 h

With potassium hydroxide; potassium permanganate; sodium periodate; chloro-trimethyl-silane; diphenyl-phosphinic acid; sodium hydrogencarbonate; triethylamine; In dichloromethane; benzene;

DOI:10.1021/jo952092u

Reference yield:

(S)-3-{(2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-5-trimethylsilanyl-pent-4-ynoyl}-4-isopropyl-oxazolidin-2-one (175656-24-3) → (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid (175656-28-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / LiOH*H₂O, H₂O₂ / H₂O; tetrahydrofuran; dimethylformamide / Ambient temperature

2: DPPA, Et₃N / benzene / 3.5 h / Heating

3: TMSCl / CH₂Cl₂ / 96 h / Ambient temperature

4: 1.) NaHCO₃, KMnO₄, NaIO₄, 2.) KOH / 1.) t-BuOH, H₂O, rt, 3 h, 2.) THF, H₂O, rt, 2.5 h

With potassium hydroxide; lithium hydroxide; potassium permanganate; sodium periodate; chloro-trimethyl-silane; diphenyl-phosphinic acid; dihydrogen peroxide; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo952092u

upstream raw materials:

{(1R,2S)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-ethyl-but-3-ynyl}-carbamic acid tert-butyl ester

(2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-pent-4-ynoic acid

(S)-3-{(2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-5-trimethylsilanyl-pent-4-ynoyl}-4-isopropyl-oxazolidin-2-one

Downstream raw materials:

(3R,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-azetidin-2-one

(2R,3R)-3-Amino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid