3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose

Base Information

Chemical Name:3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose
CAS No.:1296130-78-3
Molecular Formula:C₁₉H₂₅NO₇
Molecular Weight:379.41
Hs Code.:

Synonyms:3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose

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Chemical Property of 3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose

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Technology Process of 3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose

There total 4 articles about 3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose 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: 70.0%

: 1296130-77-2
3-O-benzyl-1,2-O-isopropylidene-7,8-dideoxy-8-azido-5,6-oxirano-β-L-glycero-D-gluco-octo-1,4-furanose

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

: 1296130-78-3
3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose

Guidance literature:: 3-O-benzyl-1,2-O-isopropylidene-7,8-dideoxy-8-azido-5,6-oxirano-β-L-glycero-D-gluco-octo-1,4-furanose; With triphenylphosphine; In tetrahydrofuran; water; at 20 ℃; for 15h; Inert atmosphere;

benzyl chloroformate; With sodium hydrogencarbonate; In tetrahydrofuran; water; toluene; at 30 ℃; for 15h; Inert atmosphere;
DOI:10.1016/j.tet.2011.02.030

Reference yield:

: 1296130-75-0
8-bromo-3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5-eno-1,4-furanose

: 1296130-78-3
3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium azide / acetone / 8 h / Inert atmosphere; Reflux

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 25 °C / Inert atmosphere

3.1: triphenylphosphine / tetrahydrofuran; water / 15 h / 20 °C / Inert atmosphere

3.2: 15 h / 30 °C / Inert atmosphere

With sodium azide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetone; 3.1: Staudinger reaction;
DOI:10.1016/j.tet.2011.02.030

Reference yield:

: 1296130-76-1
8-azido-3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5-eno-1,4-furanose

: 1296130-78-3
3-O-benzyl-(8-N,6-O-carbonyl)-7,8-dideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-octofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 25 °C / Inert atmosphere

2.1: triphenylphosphine / tetrahydrofuran; water / 15 h / 20 °C / Inert atmosphere

2.2: 15 h / 30 °C / Inert atmosphere

With 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; 2.1: Staudinger reaction;
DOI:10.1016/j.tet.2011.02.030