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

Base Information

Chemical Name:8-bromo-3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5-eno-1,4-furanose
CAS No.:1296130-75-0
Molecular Formula:C₁₈H₂₃BrO₄
Molecular Weight:383.282
Hs Code.:

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

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Chemical Property of 8-bromo-3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5-eno-1,4-furanose

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Technology Process of 8-bromo-3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5-eno-1,4-furanose

There total 1 articles about 8-bromo-3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5-eno-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: 71.0%

: 5162-44-7
1-bromo-4-butene

: 19877-13-5
3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

: 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

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 27 - 30 ℃; for 24h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.02.030

Reference yield: 88.0%

: 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

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

Guidance literature:: With sodium azide; In acetone; for 8h; Inert atmosphere; Reflux;
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

: C₂₃H₂₇NO₇

Guidance literature:: Multi-step reaction with 5 steps

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

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 25 °C / Inert atmosphere

3: palladium 10% on activated carbon; ammonium formate / ethanol / 26 h / Inert atmosphere; Reflux

4: sodium hydrogencarbonate / ethanol; water; toluene / 12 h / 20 °C / Inert atmosphere

5: water; trifluoroacetic acid / 5.5 h / 0 - 25 °C / Inert atmosphere

With sodium azide; palladium 10% on activated carbon; water; ammonium formate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In ethanol; dichloromethane; water; acetone; toluene;
DOI:10.1016/j.tet.2011.02.030