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

Base Information

Chemical Name:methyl 4-((3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)butanoate
CAS No.:863028-27-7
Molecular Formula:C₃₇H₄₇NO₉
Molecular Weight:649.781
Hs Code.:

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

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

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

There total 4 articles about methyl 4-((3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)butanoate 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: 99.0%

: 1072440-25-5
tert-butyl (2R,3R,4S,4aS,7S,9aR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-6-oxooctahydro-2H-pyrano[3,2-b]oxepin-7-ylcarbamate

: 863028-27-7
methyl 4-((3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)butanoate

Guidance literature:: With methanol; potassium carbonate; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol802009v

Reference yield: 87.0%

: 863028-32-4
methyl (2S,6S,7R,8R,9R,E)-7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate

: 863028-27-7
methyl 4-((3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)butanoate

Guidance literature:: methyl (2S,6S,7R,8R,9R,E)-7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate; With mercury(II) trifluoroacetate; In tetrahydrofuran; at 20 ℃; for 2.5h;

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

: 863028-27-7
methyl 4-((3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-(2S)-2-(tert-butoxycarbonylamino)butanoate

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: 69 percent / Grudds generation 2 catalyst / CH₂Cl₂ / 20 h / Heating

3.1: mercury(II) trifluoroacetate / tetrahydrofuran / 2.5 h / 20 °C

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

3.3: 87 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