phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate

Base Information

• Chemical Name: phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate
• CAS No.: 143601-50-7
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391

Synonyms:phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate

Chemical Property of phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate

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Technology Process of phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate

There total 10 articles about phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]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: 95.0%

methyl 4-oxo-6-phenyl-(5S)-5-[[(phenylmethoxy)carbonyl]amino]hexanoate (866563-64-6) → phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate (143601-50-7)

Guidance literature:

With (S)-alpine-hydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo060296c

Reference yield: 80.0%

(E)-(4S,5S)-5-Benzyloxycarbonylamino-4-hydroxy-6-phenyl-hex-2-enoic acid methyl ester (882400-17-1) → phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate (143601-50-7)

Guidance literature:

(E)-(4S,5S)-5-Benzyloxycarbonylamino-4-hydroxy-6-phenyl-hex-2-enoic acid methyl ester; With sodium tetrahydroborate; nickel dichloride; In methanol;

With toluene-4-sulfonic acid; In toluene; Heating;

DOI:10.1055/s-2005-921907

Reference yield: 79.0%

butyl 4-oxo-6-phenyl-(5S)-5-[[(phenylmethoxy)carbonyl]amino]hexanoate (521305-88-4) → butyl (4S)-4-hydroxy-6-phenyl-(5S)-5-[[(phenylmethoxy)carbonyl]amino]hexanoate + phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate (143601-50-7)

Guidance literature:

With (S)-alpine-hydride; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1021/jo060296c

upstream raw materials:

(S)-5-Benzyloxycarbonylamino-4-oxo-6-phenyl-hexanoic acid ethyl ester

methyl 4-oxo-6-phenyl-(5S)-5-[[(phenylmethoxy)carbonyl]amino]hexanoate

butyl 4-oxo-6-phenyl-(5S)-5-[[(phenylmethoxy)carbonyl]amino]hexanoate

(E)-(4S,5S)-5-Benzyloxycarbonylamino-4-hydroxy-6-phenyl-hex-2-enoic acid methyl ester

Downstream raw materials:

[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

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

3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid

3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid tert-butyl ester

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