(S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid (2R,3S,5R)-3-(4-chloro-benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Base Information

Chemical Name:(S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid (2R,3S,5R)-3-(4-chloro-benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
CAS No.:1053642-99-1
Molecular Formula:C₂₆H₃₃ClFN₃O₈S
Molecular Weight:602.081
Hs Code.:

(S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid (2R,3S,5R)-3-(4-chloro-benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

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Chemical Property of (S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid (2R,3S,5R)-3-(4-chloro-benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

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Technology Process of (S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid (2R,3S,5R)-3-(4-chloro-benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

There total 3 articles about (S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid (2R,3S,5R)-3-(4-chloro-benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl 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:

: 1-[(2R,4S,5R)-4-(4-Chloro-benzyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione

: 1053642-99-1
(S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid (2R,3S,5R)-3-(4-chloro-benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 0.5 N HCl / methanol / 2 h / Ambient temperature

2: pivaloyl chloride, Et₃N / N,N-dimethyl-acetamide / 0.5 h / Ambient temperature

With hydrogenchloride; pivaloyl chloride; triethylamine; In methanol; N,N-dimethyl acetamide;
DOI:10.1248/cpb.44.150

Reference yield:

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 1053642-99-1
(S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyric acid (2R,3S,5R)-3-(4-chloro-benzyloxy)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / pyridine / 0.5 h / 100 °C

2: 1.) NaH, 2.) NaI / 1.) THF, 50 deg C, 30 min, 2.) THF, 50 deg C, overnight

3: 0.5 N HCl / methanol / 2 h / Ambient temperature

4: pivaloyl chloride, Et₃N / N,N-dimethyl-acetamide / 0.5 h / Ambient temperature

With pyridine; hydrogenchloride; pivaloyl chloride; sodium hydride; triethylamine; sodium iodide; In methanol; N,N-dimethyl acetamide;
DOI:10.1248/cpb.44.150