(3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside

Base Information

Chemical Name:(3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside
CAS No.:854654-35-6
Molecular Formula:C₄₅H₅₁BrO₉
Molecular Weight:815.799
Hs Code.:

(3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside

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Chemical Property of (3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside

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Technology Process of (3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside

There total 5 articles about (3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-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:

: 854654-33-4
[3,7-anhydro-8-O-(4-toluenesulfonyl)-1,2,6-trideoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl]-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside

: 854654-35-6
(3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside

Guidance literature:: With sodium bromide; In N,N-dimethyl-formamide; at 70 ℃;
DOI:10.1016/j.tetasy.2005.02.027

Reference yield:

: 854654-27-6
3,7-anhydro-8-O-tert-butyldiphenylsilyl-1,2-dideoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol

: 854654-35-6
(3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 53 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 0 °C

2: 61 percent / tetrabutylammonium fluoride / tetrahydrofuran / 96 h / 20 °C

3: 83 percent / 4-dimethylaminopyridine; pyridine / 120 h / 20 °C

4: NaBr / dimethylformamide / 70 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4: Finkelstein exchange reaction;
DOI:10.1016/j.tetasy.2005.02.027

Reference yield:

: 3,7-anhydro-8-O-tert-butyldiphenylsilyl-1,2-dideoxy-D-glycero-D-galacto-oct-1-enitol

: 854654-35-6
(3,7-anhydro-8-bromo-1,2,6,8-tetradeoxy-4,5-di-O-isopropylidene-D-glycero-D-galacto-oct-1-enitol-6-yl)-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / p-toluenesulfonic acid / acetone

2: 53 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 0 °C

3: 61 percent / tetrabutylammonium fluoride / tetrahydrofuran / 96 h / 20 °C

4: 83 percent / 4-dimethylaminopyridine; pyridine / 120 h / 20 °C

5: NaBr / dimethylformamide / 70 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; sodium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 5: Finkelstein exchange reaction;
DOI:10.1016/j.tetasy.2005.02.027