N-tert-butoxycarbonyl-(2S,3R)-3-tert-butyldimethylsiloxyhomoserine benzyl ester

Base Information

• Chemical Name: N-tert-butoxycarbonyl-(2S,3R)-3-tert-butyldimethylsiloxyhomoserine benzyl ester
• CAS No.: 144704-72-3
• Molecular Formula: C₂₂H₃₇NO₆Si
• Molecular Weight: 439.624
• Mol file: 144704-72-3.mol

Synonyms:

Chemical Property of N-tert-butoxycarbonyl-(2S,3R)-3-tert-butyldimethylsiloxyhomoserine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butoxycarbonyl-(2S,3R)-3-tert-butyldimethylsiloxyhomoserine benzyl ester

There total 8 articles about N-tert-butoxycarbonyl-(2S,3R)-3-tert-butyldimethylsiloxyhomoserine benzyl ester 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:

di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-(2S,3R)-3-tert-butyldimethylsiloxyhomoserine benzyl ester (144704-72-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / sat. aq. NaHCO₃ / dioxane / 8 h / Ambient temperature

2: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

3: RuCl₃, NaIO₄ / ethyl acetate; acetonitrile; H₂O / 27 h / Ambient temperature

4: Et₃N, aq. MeOH

5: KHCO₃

6: imidazole

7: AcOH-THF-H₂O (13:7:3)

With tetrahydrofuran; 1H-imidazole; methanol; dmap; ruthenium trichloride; sodium periodate; sodium hydrogencarbonate; potassium hydrogencarbonate; acetic acid; triethylamine; In 1,4-dioxane; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)88039-X

Reference yield:

(2R,3R)-3-tert-butoxycarbonylamino-1,2-diacetoxy-3-phenylpropane (153704-76-8) → N-tert-butoxycarbonyl-(2S,3R)-3-tert-butyldimethylsiloxyhomoserine benzyl ester (144704-72-3)

Guidance literature:

Multi-step reaction with 5 steps

1: RuCl₃, NaIO₄ / ethyl acetate; acetonitrile; H₂O / 27 h / Ambient temperature

2: Et₃N, aq. MeOH

3: KHCO₃

4: imidazole

5: AcOH-THF-H₂O (13:7:3)

With tetrahydrofuran; 1H-imidazole; methanol; ruthenium trichloride; sodium periodate; potassium hydrogencarbonate; acetic acid; triethylamine; In water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)88039-X

Reference yield:

benzyl bromide (100-39-0) + (2S,3R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-butyric acid; compound with triethyl-amine → N-tert-butoxycarbonyl-(2S,3R)-3-tert-butyldimethylsiloxyhomoserine benzyl ester (144704-72-3) + N-tert-butoxycarbonyl-(2R,3R)-3-hydroxyhomoserine benzyl ester (144704-73-4)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; for 18h; Yield given. Yields of byproduct given;

DOI:10.1016/S0957-4166(00)86041-3

upstream raw materials:

benzyl bromide

di-tert-butyl dicarbonate

(2S,3R)-2-tert-butoxycarbonylamino-3,4-diacetoxybutanoic acid

(2R,3R)-3-tert-butoxycarbonylamino-1,2-diacetoxy-3-phenylpropane

Downstream raw materials:

benzyl N-<(2S,2'S,3S)-3'-tert-butoxycarbonylamino-3'-benzyloxycarbonyl-2'-tert-butyldimethylsiloxypropyl>-2-azetidinecarboxylate