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

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-deoxy-2-[(1R/S)-2,5-(benzylimino)-1,2,5-trideoxy-3,4-O-isopropylidene-1-(phenylthio)-L-ribitol-1C-yl]-α-D-ribo-hexopyranosid-3-ulose
CAS No.:914784-25-1
Molecular Formula:C₃₅H₃₉NO₇S
Molecular Weight:617.763
Hs Code.:

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

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

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Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-[(1R/S)-2,5-(benzylimino)-1,2,5-trideoxy-3,4-O-isopropylidene-1-(phenylthio)-L-ribitol-1C-yl]-α-D-ribo-hexopyranosid-3-ulose

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-[(1R/S)-2,5-(benzylimino)-1,2,5-trideoxy-3,4-O-isopropylidene-1-(phenylthio)-L-ribitol-1C-yl]-α-D-ribo-hexopyranosid-3-ulose

There total 4 articles about methyl 4,6-O-benzylidene-2-deoxy-2-[(1R/S)-2,5-(benzylimino)-1,2,5-trideoxy-3,4-O-isopropylidene-1-(phenylthio)-L-ribitol-1C-yl]-α-D-ribo-hexopyranosid-3-ulose 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: 91.0%

: 914784-21-7
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-erythro-hexopyranosid-3-ulose

: 108-98-5
thiophenol

: 914784-25-1
methyl 4,6-O-benzylidene-2-deoxy-2-[(1R/S)-2,5-(benzylimino)-1,2,5-trideoxy-3,4-O-isopropylidene-1-(phenylthio)-L-ribitol-1C-yl]-α-D-ribo-hexopyranosid-3-ulose

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
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

: 914784-25-1
methyl 4,6-O-benzylidene-2-deoxy-2-[(1R/S)-2,5-(benzylimino)-1,2,5-trideoxy-3,4-O-isopropylidene-1-(phenylthio)-L-ribitol-1C-yl]-α-D-ribo-hexopyranosid-3-ulose

Guidance literature:: Multi-step reaction with 2 steps

1: 49 percent / Et₂NSF₃ / CH₂Cl₂ / 4 h / -78 - 25 °C

2: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With diethylamino-sulfur trifluoride; triethylamine; In dichloromethane;
DOI:10.1002/ejoc.200600199

Reference yield:

: 63598-31-2
methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

: 914784-25-1
methyl 4,6-O-benzylidene-2-deoxy-2-[(1R/S)-2,5-(benzylimino)-1,2,5-trideoxy-3,4-O-isopropylidene-1-(phenylthio)-L-ribitol-1C-yl]-α-D-ribo-hexopyranosid-3-ulose

Guidance literature:: Multi-step reaction with 3 steps

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

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

2.1: 49 percent / Et₂NSF₃ / CH₂Cl₂ / 4 h / -78 - 25 °C

3.1: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With diethylamino-sulfur trifluoride; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/ejoc.200600199