(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine

Base Information

Chemical Name:(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine
CAS No.:161275-60-1
Molecular Formula:C₃₄H₃₇N₃O₉S
Molecular Weight:663.748
Hs Code.:

Synonyms:(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine

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Chemical Property of (3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine

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Technology Process of (3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine

There total 5 articles about (3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine 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: 88.0%

: 161275-59-8
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-1-(prop-2-en-1-yloxy)carbonyl-5-(methanesulfonyloxy)methylpyrrolidine

: 161275-60-1
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.166667h;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 560130-29-2
4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

: 161275-60-1
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 27 percent / DMAP / tetrahydrofuran / 0.17 h / 20 °C

2: 15 percent / DMAP / toluene / 2 h / 50 °C

3: 79 percent / HF-pyridine complex / pyridine / 1.5 h / 0 - 20 °C

4: 83 percent / PDC; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

5: p-TsOH*H₂O / tetrahydrofuran / 0.5 h / 20 °C

6: 24.9 mg / diethyl ether; tetrahydrofuran / 12 h / 20 °C

7: 88 percent / Ph₃P; AcOH; Pd(PPh₃)4 / tetrahydrofuran / 0.17 h / 20 °C

With dmap; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4 A molecular sieve; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; triphenylphosphine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0040-4020(03)00378-8

Reference yield:

: 228120-04-5
(E)-4-[(3R,4R,5S)-1-allyloxycarbonyl-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one

: 161275-60-1
(3R,4R,5S)-2-[(Z)-1-benzoylamino-1-(((Z)-4-methoxybut-3-en-2-on-3-yl)carbamoyl)methylidene]-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 15 percent / DMAP / toluene / 2 h / 50 °C

2: 79 percent / HF-pyridine complex / pyridine / 1.5 h / 0 - 20 °C

3: 83 percent / PDC; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

4: p-TsOH*H₂O / tetrahydrofuran / 0.5 h / 20 °C

5: 24.9 mg / diethyl ether; tetrahydrofuran / 12 h / 20 °C

6: 88 percent / Ph₃P; AcOH; Pd(PPh₃)4 / tetrahydrofuran / 0.17 h / 20 °C

With dmap; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4 A molecular sieve; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; triphenylphosphine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0040-4020(03)00378-8