5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-β-L-ido-oct-1,4-furanose

Base Information

Chemical Name:5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-β-L-ido-oct-1,4-furanose
CAS No.:329361-93-5
Molecular Formula:C₁₉H₂₅NO₆
Molecular Weight:363.411
Hs Code.:

Synonyms:5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-β-L-ido-oct-1,4-furanose

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Chemical Property of 5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-β-L-ido-oct-1,4-furanose

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Technology Process of 5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-β-L-ido-oct-1,4-furanose

There total 6 articles about 5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-β-L-ido-oct-1,4-furanose 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:

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

: 91-00-9
Benzhydrylamine

: 330970-44-0
4-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-oxo-butyraldehyde

: 115438-59-0
5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-α-D-gluco-oct-1,4-furanose

: 329361-93-5
5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-β-L-ido-oct-1,4-furanose

Guidance literature:: Benzhydrylamine; 4-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-oxo-butyraldehyde; With sodium cyanoborohydride; acetic acid; In methanol; at -78 - 20 ℃; for 12h;

With hydrogen; palladium on activated charcoal; In methanol; for 20h; under 4137.18 Torr;

benzyl chloroformate; With sodium hydrogencarbonate; In ethanol; water; for 2h;
DOI:10.1016/S0040-4039(00)02103-1

Reference yield:

: 690981-80-7
(S)-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

: 329361-93-5
5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-β-L-ido-oct-1,4-furanose

Guidance literature:: Multi-step reaction with 3 steps

1.1: mercury acetate / tetrahydrofuran; H₂O / 18 h / 20 °C

1.2: 72 percent / NaBH₄ / tetrahydrofuran; H₂O

2.1: H₂ / Pd-C / methanol / 16 h / 20 °C / 4137.18 Torr

3.1: 0.22 g / aq. NaHCO₃ / ethanol / 2 h / 25 °C

With mercury(II) diacetate; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;
DOI:10.3390/10080893