2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole

Base Information

Chemical Name:2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole
CAS No.:236388-80-0
Molecular Formula:C₄₅H₄₅NO₆
Molecular Weight:695.855
Hs Code.:

Synonyms:2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole

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Chemical Property of 2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole

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Technology Process of 2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole

There total 4 articles about 2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole 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: 50.0%

: 140397-46-2
(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methanal

: (R)-4-((2-phenyl-2-oxazolininyl)methyl)triphenylphosphonium iodide

: 236388-80-0
2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole

Guidance literature:: With n-butyllithium; 4 Angstroem MS; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 2h;
DOI:10.1021/jo990398l

Reference yield:

: 137649-96-8
(S)-2-phenyl-4-hydroxymethyl-4,5-dihydrooxazole

: 236388-80-0
2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / PPh₃, imidazole, I₂ / toluene / 0.5 h / 80 °C

2: 90 percent / 1 h / 120 °C

3: 50 percent / n-BuLi, 4 Angstroem MS / tetrahydrofuran; hexane / 2 h / -78 - -20 °C

With 1H-imidazole; n-butyllithium; 4 Angstroem MS; iodine; triphenylphosphine; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jo990398l

Reference yield:

: 105308-52-9
(R)-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

: 236388-80-0
2-Phenyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-4,5-dihydro-oxazole

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / -50 °C

2: 80 percent / PPh₃, imidazole, I₂ / toluene / 0.5 h / 80 °C

3: 90 percent / 1 h / 120 °C

4: 50 percent / n-BuLi, 4 Angstroem MS / tetrahydrofuran; hexane / 2 h / -78 - -20 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; 4 Angstroem MS; iodine; triphenylphosphine; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jo990398l