ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate

Base Information

Chemical Name:ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate
CAS No.:294172-56-8
Molecular Formula:C₁₉H₂₅NO₆
Molecular Weight:363.411
Hs Code.:

Synonyms:ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate

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Chemical Property of ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate

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Technology Process of ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate

There total 1 articles about ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate 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: 88.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 149342-29-0
Ethyl 1,4,5-trideoxy-3,6-imino-4,5-O-isopropylidene-L-arabino-hexonate

: 294172-56-8
ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate

Guidance literature:: With sodium hydrogencarbonate; In ethanol; water; at 20 ℃; for 3h;
DOI:10.1080/07328300008544099

Reference yield:

: 294172-56-8
ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate

: 294172-62-6
(E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(tert-butoxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-erythro-hexopyran-4-olose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1.44 g / H₂ / Pd/C / methanol / 1 h / 20 °C

2.1: 83 percent / (i-Bu)2AlH / CH₂Cl₂ / 3.5 h / -78 °C

3.1: BuLi; HN(SiMe₃)2 / hexane; tetrahydrofuran / 2 h / -78 °C

3.2: tetrahydrofuran; hexane / 15.5 h / -100 - -60 °C

3.3: 78 percent / SiO₂ / CH₂Cl₂ / 0.25 h / 20 °C

With n-butyllithium; hydrogen; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Hydrogenolysis / 2.1: Reduction / 3.1: deprotonation / 3.2: Addition / 3.3: Dehydration;
DOI:10.1080/07328300008544099

Reference yield:

: 294172-56-8
ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate

: 294172-63-7
(Z)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(tert-butoxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-xylo-hexopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1.44 g / H₂ / Pd/C / methanol / 1 h / 20 °C

2.1: 83 percent / (i-Bu)2AlH / CH₂Cl₂ / 3.5 h / -78 °C

3.1: BuLi; HN(SiMe₃)2 / hexane; tetrahydrofuran / 2 h / -78 °C

3.2: tetrahydrofuran; hexane / 15.5 h / -100 - -60 °C

3.3: 78 percent / SiO₂ / CH₂Cl₂ / 0.25 h / 20 °C

4.1: 89 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; hydrogen; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Hydrogenolysis / 2.1: Reduction / 3.1: deprotonation / 3.2: Addition / 3.3: Dehydration / 4.1: Reduction;
DOI:10.1080/07328300008544099