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

Base Information

Chemical Name:methyl (2S,6S,7R,8R,9R,E)-7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate
CAS No.:863028-32-4
Molecular Formula:C₃₇H₄₇NO₉
Molecular Weight:649.781
Hs Code.:

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

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Chemical Property of methyl (2S,6S,7R,8R,9R,E)-7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate

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Technology Process of methyl (2S,6S,7R,8R,9R,E)-7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate

There total 2 articles about methyl (2S,6S,7R,8R,9R,E)-7,8,10-tris(benzyloxy)-2-(tert-butoxycarbonylamino)-6,9-dihydroxydec-4-enoate 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: 69.0%

: 89985-87-5
methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate

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

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

: (E)-(2R,3R,4R,5S,8S,9R,10R,11R)-1,3,4,9,10,12-Hexakis-benzyloxy-dodec-6-ene-2,5,8,11-tetraol

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 20h; Heating;
DOI:10.1021/ol051341q

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / tetrahydrofuran / 6 h / 20 °C

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

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

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