(E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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

Base Information

Chemical Name:(E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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
CAS No.:294172-58-0
Molecular Formula:C₃₀H₃₃NO₈
Molecular Weight:535.594
Hs Code.:

(E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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

Synonyms:(E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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

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Chemical Property of (E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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

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Technology Process of (E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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

There total 4 articles about (E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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 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: 94.0%

: 123823-24-5
1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose

: 294172-57-9
3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose

: 294172-58-0
(E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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:: 1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose; In tetrahydrofuran; hexane; at -100 - -60 ℃; for 15.5h;

With silica gel; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1080/07328300008544099

Reference yield:

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

: 294172-58-0
(E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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: 88 percent / NaHCO₃ / H₂O; ethanol / 3 h / 20 °C

2.1: 54 percent / (i-Bu)2AlH / CH₂Cl₂ / 2 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: 94 percent / SiO₂ / CH₂Cl₂ / 15 h / 20 °C

With n-butyllithium; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; 1.1: Condensation / 2.1: Reduction / 3.1: deprotonation / 3.2: Addition / 3.3: Dehydration;
DOI:10.1080/07328300008544099

Reference yield:

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

: 294172-58-0
(E)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)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: 88 percent / NaHCO₃ / H₂O; ethanol / 3 h / 20 °C

2.1: 54 percent / (i-Bu)2AlH / CH₂Cl₂ / 2 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: 94 percent / SiO₂ / CH₂Cl₂ / 15 h / 20 °C

With n-butyllithium; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; 1.1: Condensation / 2.1: Reduction / 3.1: deprotonation / 3.2: Addition / 3.3: Dehydration;
DOI:10.1080/07328300008544099