(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

Base Information

Chemical Name:(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
CAS No.:294172-63-7
Molecular Formula:C₂₇H₃₇NO₈
Molecular Weight:503.593
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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: 89.0%

: 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

: 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:: With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1080/07328300008544099

Reference yield:

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

: 294172-63-7
(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 5 steps

1.1: 88 percent / NaHCO₃ / H₂O; ethanol / 3 h / 20 °C

2.1: 1.44 g / H₂ / Pd/C / methanol / 1 h / 20 °C

3.1: 83 percent / (i-Bu)2AlH / CH₂Cl₂ / 3.5 h / -78 °C

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

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

4.3: 78 percent / SiO₂ / CH₂Cl₂ / 0.25 h / 20 °C

5.1: 89 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; 1.1: Condensation / 2.1: Hydrogenolysis / 3.1: Reduction / 4.1: deprotonation / 4.2: Addition / 4.3: Dehydration / 5.1: Reduction;
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