tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate

Base Information

Chemical Name:tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate
CAS No.:452977-10-5
Molecular Formula:C₁₈H₂₀N₄O₅
Molecular Weight:372.381
Hs Code.:

Synonyms:tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate

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Chemical Property of tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate

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Technology Process of tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate

There total 6 articles about tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}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: 26.0%

: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

: (3R,3aS,6aR)-(Hexahydro-furo[2,3-b]furan-3-yl)-acetic acid

: 452977-10-5
tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate

: 452977-14-9
tert-butyl N-{(1S)-1-[(3S,3aS,6aR)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate

Guidance literature:: (3R,3aS,6aR)-(Hexahydro-furo[2,3-b]furan-3-yl)-acetic acid; With pivaloyl chloride; triethylamine;

(S)-4-Benzyl-2-oxazolidinone; With n-butyllithium; at -78 ℃; for 2h;

With 2,4,6-Triisopropylbenzenesulfonyl azide; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(02)00448-3

Reference yield:

: (3R,3aS,6aR)-(Hexahydro-furo[2,3-b]furan-3-yl)-acetic acid ethyl ester

: 452977-10-5
tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 79 percent / NaOH (4N) / ethanol / 1.5 h

2.1: PivCl; Et₃N

2.2: nBuLi / 2 h / -78 °C

2.3: 26 percent / KN(TMS)2; trisyl azide / tetrahydrofuran / -78 °C

With sodium hydroxide; pivaloyl chloride; triethylamine; In ethanol;
DOI:10.1016/S0040-4039(02)00448-3

Reference yield:

: (E)-4-((2S,3R)-3-Bromo-tetrahydro-furan-2-yloxy)-but-2-enoic acid ethyl ester

: 452977-10-5
tert-butyl N-{(1S)-1-[(3R,3aR,6aS)-perhydrofuro[2,3-b]furan-3-yl]-2-[(4S)-4-benzyl-2-oxo-1,3-oxazolan-3-yl]-2-oxoethyl}carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 81 percent / nBu₃SnH; AIBN / benzene / 4 h / 80 °C

2.1: 79 percent / NaOH (4N) / ethanol / 1.5 h

3.1: PivCl; Et₃N

3.2: nBuLi / 2 h / -78 °C

3.3: 26 percent / KN(TMS)2; trisyl azide / tetrahydrofuran / -78 °C

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pivaloyl chloride; triethylamine; In ethanol; benzene;
DOI:10.1016/S0040-4039(02)00448-3