(Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl ester

Base Information

Chemical Name:(Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl ester
CAS No.:192370-37-9
Molecular Formula:C₂₇H₃₄N₆O₆
Molecular Weight:538.604
Hs Code.:

Synonyms:(Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl ester

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Chemical Property of (Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl ester

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Technology Process of (Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl ester

There total 11 articles about (Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl 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:

: 51442-80-9
5-(tetrahydro-2H-pyran-2-yloxy)-2-pentyn-1-ol

: 192370-37-9
(Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) Red-Al, 2.) NIS / 1.) THF, 0 deg C to room temp., 2.) THF, -78 deg C, 10 min

2: 97 percent / imidazole / tetrahydrofuran / 16 h / Ambient temperature

3: 1.) Zn, CH₂(OCH₃)2, 2.) 8 molpercent Pd(PPh₃)4, DMPU / 1.) reflux, 30 min, 2.) 65 deg C, 4 h

4: p-TSA / ethanol / Ambient temperature

5: 74 percent / DIAD, PPh₃, Zn(N₃)2*2pyridine / toluene / 3 h / Ambient temperature

6: 75 percent / HF*pyridine / pyridine; acetonitrile / 2.5 h / Ambient temperature

7: 67 percent / DEAD, PPh₃ / tetrahydrofuran / 6 h / Ambient temperature

8: H₂ / Lindlar catalyst / ethanol / 48 h / Ambient temperature

10: 60 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

11: H₂ / Lindlar catalyst / ethanol / 4 h / Ambient temperature

12: CH₂Cl₂ / 16 h / Ambient temperature

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; Zn(N₃)2/bis-pyridine complex; Dimethoxymethane; di-isopropyl azodicarboxylate; hydrogen; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; zinc; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(97)00871-X

Reference yield:

: 121353-11-5
(Z)-3-iodo-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-en-1-ol

: 192370-37-9
(Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 97 percent / imidazole / tetrahydrofuran / 16 h / Ambient temperature

2: 1.) Zn, CH₂(OCH₃)2, 2.) 8 molpercent Pd(PPh₃)4, DMPU / 1.) reflux, 30 min, 2.) 65 deg C, 4 h

3: p-TSA / ethanol / Ambient temperature

4: 74 percent / DIAD, PPh₃, Zn(N₃)2*2pyridine / toluene / 3 h / Ambient temperature

5: 75 percent / HF*pyridine / pyridine; acetonitrile / 2.5 h / Ambient temperature

6: 67 percent / DEAD, PPh₃ / tetrahydrofuran / 6 h / Ambient temperature

7: H₂ / Lindlar catalyst / ethanol / 48 h / Ambient temperature

9: 60 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

10: H₂ / Lindlar catalyst / ethanol / 4 h / Ambient temperature

11: CH₂Cl₂ / 16 h / Ambient temperature

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; Zn(N₃)2/bis-pyridine complex; Dimethoxymethane; di-isopropyl azodicarboxylate; hydrogen; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triphenylphosphine; zinc; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(97)00871-X

Reference yield:

: 192370-33-5
(Z)-3-(2-Azido-ethyl)-5-hydroxy-pent-3-enoic acid ethyl ester

: 192370-37-9
(Z)-5-(6-Benzyloxycarbonylamino-purin-9-yl)-3-(2-tert-butoxycarbonylamino-ethyl)-pent-3-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 67 percent / DEAD, PPh₃ / tetrahydrofuran / 6 h / Ambient temperature

2: H₂ / Lindlar catalyst / ethanol / 48 h / Ambient temperature

4: 60 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

5: H₂ / Lindlar catalyst / ethanol / 4 h / Ambient temperature

6: CH₂Cl₂ / 16 h / Ambient temperature

With sodium azide; hydrogen; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)00871-X