(3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate

Base Information

Chemical Name:(3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate
CAS No.:1309766-87-7
Molecular Formula:C₄₈H₅₀N₂O₆S
Molecular Weight:783.001
Hs Code.:

Synonyms:(3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate

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Chemical Property of (3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate

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Technology Process of (3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate

There total 8 articles about (3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate 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: 92.0%

: C₁₁H₂₁NO₃*ClH

: 167015-11-4
Fmoc-D-Cys(Trt)-OH

: allyl (3S,4R,5S)-4[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(tritylthio)propionylamino]-3-hydroxy-5-methylheptanoate

: 1309766-87-7
(3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;
DOI:10.1039/c0ob01169j

Reference yield:

: 1309766-93-5
(3S,4R,5S)-allyl 4-(tert-butoxycarbonylamino)-3-hydroxy-5-methylheptanoate

: 1309766-87-7
(3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 3 h

2.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C

2.2: 0 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ol202197q

Reference yield:

: 1351107-20-4
(4R,5S)-allyl 4-(tert-butoxycarbonylamino)-5-methyl-3-oxoheptanoate

: 1309766-87-7
(3S,4R,5S)-allyl 4-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanamido)-3-hydroxy-5-methylheptanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium borohydride / methanol / 0.83 h / -78 - 0 °C

2.1: trifluoroacetic acid / dichloromethane / 3 h

3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C

3.2: 0 °C

With potassium borohydride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/ol202197q