[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

Base Information

Chemical Name:[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
CAS No.:854654-33-4
Molecular Formula:C₅₂H₅₈O₁₂S
Molecular Weight:907.091
Hs Code.:

[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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of [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

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Technology Process of [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

There total 4 articles about [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 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: 83.0%

: 854654-31-2
(3,7-anhydro-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

: 98-59-9
p-toluenesulfonyl chloride

: 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

Guidance literature:: With pyridine; dmap; at 20 ℃; for 120h;
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

: 854654-33-4
[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

Guidance literature:: Multi-step reaction with 3 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

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
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

: 854654-33-4
[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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1016/j.tetasy.2005.02.027