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

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Chemical Name: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
CAS No.:944412-75-3
Molecular Formula:C₅₅H₅₆N₂O₁₃S
Molecular Weight:985.121
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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: 91.0%

: 944412-79-7
C₃₄H₄₀N₂O₁₂

: 34914-36-8
2-(triphenylmethylthio)ethanoic acid

: 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:: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield:

: 73731-37-0
Fmoc-Thr-OH

: 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 4 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

3.1: 94 percent / Zn; AcOH / 4 h / 20 °C

4.1: 877.7 mg / HBTU; iPr₂NEt / dimethylformamide / 2 h / 20 °C

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

Reference yield:

: 136523-92-7
N-(9-fluorenylmethoxycarbonyl)-L-threonine allyl ester

: 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 3 steps

1: 45.4 percent / TMSOTf / CH₂Cl₂ / 0.75 h / -78 °C

2: 94 percent / Zn; AcOH / 4 h / 20 °C

3: 877.7 mg / HBTU; iPr₂NEt / dimethylformamide / 2 h / 20 °C

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