{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester
• CAS No.: 333405-44-0
• Molecular Formula: C₂₀H₂₈N₄O₄
• Molecular Weight: 388.467
• Mol file: 333405-44-0.mol

Synonyms:{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

Chemical Property of {(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

There total 4 articles about {(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl 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:

Methanesulfonic acid 3-[(3R,5S)-5-((S)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propyl ester → {(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester (333405-44-0)

Guidance literature:

With sodium azide; tetrabutylammomium bromide; In water; toluene; for 3h; Heating;

DOI:10.1021/ol015612i

Reference yield:

tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate (133333-27-4) → {(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester (333405-44-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

1.2: 62 percent / DMPU / tetrahydrofuran / 1.75 h / -78 - -50 °C

2.1: catecholborane; Rh(PPh₃)3Cl / tetrahydrofuran / 0.67 h / 20 °C

2.2: 70 percent / aq. H₂O₂; phosphate buffer / tetrahydrofuran; ethanol / 0 - 20 °C / pH 7.2

3.1: triethylamine / toluene / 0 - 20 °C

4.1: NaN₃; Bu₄NBr / H₂O; toluene / 3 h / Heating

With Wilkinson's catalyst; sodium azide; tetrabutylammomium bromide; triethylamine; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; In tetrahydrofuran; water; toluene;

DOI:10.1021/ol015612i

Reference yield:

{(1S)-1-[(4R)-4-allyl-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester (137281-77-7) → {(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester (333405-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: catecholborane; Rh(PPh₃)3Cl / tetrahydrofuran / 0.67 h / 20 °C

1.2: 70 percent / aq. H₂O₂; phosphate buffer / tetrahydrofuran; ethanol / 0 - 20 °C / pH 7.2

2.1: triethylamine / toluene / 0 - 20 °C

3.1: NaN₃; Bu₄NBr / H₂O; toluene / 3 h / Heating

With Wilkinson's catalyst; sodium azide; tetrabutylammomium bromide; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; water; toluene;

DOI:10.1021/ol015612i

upstream raw materials:

tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate

{(1S)-1-[(4R)-4-allyl-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

{(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

Downstream raw materials:

(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-(2R)-2-(3-N,N'-bis-t-boc-guanidino-propyl)-6-phenyl-hexanoic acid

C₄₆H₄₆N₄O₇H₂SiC₆H₁₄P(C₆H₅)3

(2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

[(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester