methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside
CAS No.:914784-23-9
Molecular Formula:C₂₂H₃₁NO₇
Molecular Weight:421.491
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside

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Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside

There total 4 articles about methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside 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: 82.0%

: 914784-22-8
methyl 4,6-O-benzylidene-2-deoxy-2-[(1Z)-2,5-(benzylimino)-1,2,5-trideoxy-3,4-O-isopropylidene-L-ribitol-1C-ylidene]-α-D-arabino-hexopyranoside

: 914784-23-9
methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 6h; under 760 Torr;
DOI:10.1002/ejoc.200600199

Reference yield:

: 914784-17-1
methyl 4,6-O-benzylidene-2-deoxy-2-[(1R/1S)-2,5-(benzylimino)-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1C-yl]-α-D-ribo-hexopyranosid-3-ulose

: 914784-23-9
methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 34 percent / Et₂NSF₃ / CH₂Cl₂ / 4 h / -78 - 25 °C

2: 87 percent / NaBH₄; CeCl₃ / methanol / 0.17 h

3: 82 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C / 760 Torr

With sodium tetrahydroborate; cerium(III) chloride; diethylamino-sulfur trifluoride; hydrogen; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.200600199

Reference yield:

: 914784-16-0
N-benzyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose

: 914784-23-9
methyl 4,6-O-benzylidene-2-deoxy-2-(1,2,5-trideoxy-2,5-imino-3,4-O-isopropylidene-L-ribitol-1C-yl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: KHMDS / toluene; tetrahydrofuran / 0.5 h / -40 °C

1.2: 81 percent / HMPA / tetrahydrofuran; toluene / -85 °C

2.1: 34 percent / Et₂NSF₃ / CH₂Cl₂ / 4 h / -78 - 25 °C

3.1: 87 percent / NaBH₄; CeCl₃ / methanol / 0.17 h

4.1: 82 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C / 760 Torr

With sodium tetrahydroborate; cerium(III) chloride; diethylamino-sulfur trifluoride; hydrogen; potassium hexamethylsilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1002/ejoc.200600199