3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose

Base Information

Chemical Name:3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose
CAS No.:1289557-59-0
Molecular Formula:C₁₈H₂₁NO₄S
Molecular Weight:347.435
Hs Code.:

Synonyms:3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose

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Chemical Property of 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose

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Technology Process of 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose

There total 4 articles about 3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose 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: 53.0%

: 1289557-56-7
(E)-3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-7-thiocyanato-α-D-xylo-hept-5-enfuranose

: 1289557-59-0
3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose

: 1289557-58-9
3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose

Guidance literature:: In n-heptane; at 90 ℃; for 24h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

: 108182-63-4
(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose

: 1289557-59-0
3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose

: 1289557-58-9
3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 1.75 h / 0 - 20 °C / Inert atmosphere

2: acetonitrile / 2.5 h / 20 °C / Inert atmosphere

3: n-heptane / 24 h / 90 °C / Inert atmosphere

With triethylamine; In n-heptane; dichloromethane; acetonitrile; 3: aza-Claisen rearrangement;
DOI:10.1016/j.tetasy.2011.02.004

Reference yield:

: 108788-49-4
ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

: 1289557-59-0
3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-β-L-ido-hept-6-enfuranose

: 1289557-58-9
3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-isothiocyanato-α-D-gluco-hept-6-enfuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.83 h / -13 °C / Inert atmosphere

1.2: -13 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 1.75 h / 0 - 20 °C / Inert atmosphere

3.1: acetonitrile / 2.5 h / 20 °C / Inert atmosphere

4.1: n-heptane / 24 h / 90 °C / Inert atmosphere

With diisobutylaluminium hydride; triethylamine; In n-heptane; dichloromethane; toluene; acetonitrile; 4.1: aza-Claisen rearrangement;
DOI:10.1016/j.tetasy.2011.02.004