(3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

Base Information

Chemical Name:(3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate
CAS No.:136497-87-5
Molecular Formula:C₃₄H₃₈N₄O₁₂
Molecular Weight:694.695
Hs Code.:

(3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

Synonyms:(3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

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Chemical Property of (3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

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Technology Process of (3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

There total 1 articles about (3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate 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:

: 73731-37-0
Fmoc-Thr-OH

: 136497-87-5
(3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Cs₂CO₃ / methanol / 2 h / 20 °C

1.2: 87 percent / dimethylformamide / 8 h / 20 °C

2.1: 45.4 percent / TMSOTf / CH₂Cl₂ / 0.75 h / -78 °C

With trimethylsilyl trifluoromethanesulfonate; caesium carbonate; In methanol; dichloromethane;
DOI:10.1021/ja0708971

Reference yield:

: 136497-87-5
(3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

: 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4,5-diacetoxy-6-(acetoxymethyl)-3-(2-(tritylthio)acetamido)tetrahydro-2H-pyran-2-yloxy)butanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / Zn; AcOH / 4 h / 20 °C

2: 877.7 mg / HBTU; iPr₂NEt / dimethylformamide / 2 h / 20 °C

3: 95 percent / N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran / 0.75 h / 20 °C

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja0708971

Reference yield:

: 136497-87-5
(3R,4R,5S,6S)-6-((2R,3S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate

: 944412-75-3
6-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutan-2-yloxy)-2-(acetoxymethyl)-5-(2-(tritylthio)acetamido)tetrahydro-2H-pyran-3,4-diyl diacetate

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / Zn; AcOH / 4 h / 20 °C

2: 877.7 mg / HBTU; iPr₂NEt / dimethylformamide / 2 h / 20 °C

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In N,N-dimethyl-formamide;
DOI:10.1021/ja0708971