benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate

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Chemical Name:benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate
CAS No.:863028-29-9
Molecular Formula:C₄₂H₄₉NO₉
Molecular Weight:711.852
Hs Code.:

Synonyms:benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate

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Chemical Property of benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate

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Technology Process of benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate

There total 3 articles about benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate 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: 84.0%

: 863028-36-8
benzyl (2S,5S,6R,7R,8R,E)-6,7,9-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-5,8-dihydroxynon-3-enoate

: 863028-29-9
benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate

Guidance literature:: benzyl (2S,5S,6R,7R,8R,E)-6,7,9-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-5,8-dihydroxynon-3-enoate; With mercury(II) trifluoroacetate; In tetrahydrofuran; at 20 ℃; for 2h;

With potassium chloride; In tetrahydrofuran; water; at 20 ℃; for 1h;

With sodium tetrahydroborate; triethyl borane; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/ol051341q

Reference yield:

: 37776-25-3
2,3,5-tri-O-benzyl-D-arabinose

: 863028-29-9
benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / tetrahydrofuran / 6 h / 20 °C

2.1: 62 percent / Grudds generation 2 catalyst / CH₂Cl₂ / 20 h / Heating

3.1: mercury(II) trifluoroacetate / tetrahydrofuran / 2 h / 20 °C

3.2: KCl / tetrahydrofuran; H₂O / 1 h / 20 °C

3.3: 84 percent / BEt₃; NaBH₄ / tetrahydrofuran / 1 h / -78 °C

With mercury(II) trifluoroacetate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 2.1: olefin cross-metathesis;
DOI:10.1021/ol051341q

Reference yield:

: 93125-77-0
(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol

: 863028-29-9
benzyl 3-((2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)propanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 62 percent / Grudds generation 2 catalyst / CH₂Cl₂ / 20 h / Heating

2.1: mercury(II) trifluoroacetate / tetrahydrofuran / 2 h / 20 °C

2.2: KCl / tetrahydrofuran; H₂O / 1 h / 20 °C

2.3: 84 percent / BEt₃; NaBH₄ / tetrahydrofuran / 1 h / -78 °C

With mercury(II) trifluoroacetate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 1.1: olefin cross-metathesis;
DOI:10.1021/ol051341q