tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate

Base Information

Chemical Name:tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate
CAS No.:906652-15-1
Molecular Formula:C₅₈H₈₃NO₉
Molecular Weight:938.298
Hs Code.:

Synonyms:tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate

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Chemical Property of tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate

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Technology Process of tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate

There total 11 articles about tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate 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: 80.0%

: 906651-98-7
[(S,E)-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadec-4-en-3-yl]-bis carbamic acid tert-butyl ester

: 906652-15-1
tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate

: 906652-17-3
tert-butyl (3S,4R,5S)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate

Guidance literature:: [(S,E)-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadec-4-en-3-yl]-bis carbamic acid tert-butyl ester; With disodium hydrogenphosphate; urea-hydrogen peroxide; trifluoroacetic anhydride; In dichloromethane; at -40 - 20 ℃; for 12h;

With potassium hydroxide; In ethanol; at 40 ℃; for 2h;
DOI:10.1021/ol0613057

Reference yield:

: 906651-94-3
(R,E)-2-methyl-N-(3-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)propylidene)propane-2-sulfinamide

: 906652-15-1
tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: zirconocene hydrochloride / CH₂Cl₂ / 0.08 h / 20 °C

1.2: trimethylaluminum / CH₂Cl₂ / 5 h / 0 - 20 °C

1.3: 72 percent / HCl / CH₂Cl₂; methanol; H₂O / 1 h / 20 °C

2.1: 96 percent / triethylamine; DMAP / CH₂Cl₂ / 1 h / 20 °C

3.1: 90 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

4.1: urea-hydrogen peroxide; Na₂HPO₄; trifluoroacetic anhydride / CH₂Cl₂ / 12 h / -40 - 20 °C

4.2: 80 percent / KOH / ethanol / 2 h / 40 °C

With dmap; disodium hydrogenphosphate; n-butyllithium; urea-hydrogen peroxide; zirconocene hydrochloride; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0613057

Reference yield:

: 906652-11-7
(S,E)-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadec-4-en-3-amine

: 906652-15-1
tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / triethylamine; DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: 90 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

3.1: urea-hydrogen peroxide; Na₂HPO₄; trifluoroacetic anhydride / CH₂Cl₂ / 12 h / -40 - 20 °C

3.2: 80 percent / KOH / ethanol / 2 h / 40 °C

With dmap; disodium hydrogenphosphate; n-butyllithium; urea-hydrogen peroxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0613057