benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal

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Chemical Name:benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal
CAS No.:1015075-57-6
Molecular Formula:C₃₅H₄₂O₇S₂
Molecular Weight:638.846
Hs Code.:

Synonyms:benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal

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Chemical Property of benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal

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Technology Process of benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal

There total 5 articles about benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal 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: 78.0%

: 64114-00-7
benzyl 1,3-dithiane-2-carboxylate

: 1015075-54-3
5,6-di-O-benzyl-2,3-di-O-isopropylidene-1,4-di-O-sulfate-D-mannitol

: 1015075-57-6
benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal

Guidance literature:: benzyl 1,3-dithiane-2-carboxylate; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -45 ℃; for 2h;

5,6-di-O-benzyl-2,3-di-O-isopropylidene-1,4-di-O-sulfate-D-mannitol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 20 ℃; for 2h;

With sulfuric acid; water; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 50 ℃; for 1h; pH=3; Further stages.;
DOI:10.1002/chem.200701165

Reference yield:

: 1015075-51-0
5,6-di-O-benzyl-2,3-di-O-isopropylidene-D-mannitol

: 1015075-57-6
benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal

Guidance literature:: Multi-step reaction with 2 steps

1.1: thionyl chloride; triethylamine / dichloromethane / 0.5 h / -15 °C

1.2: 0.33 h

2.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h

2.2: 2 h / 20 °C

With n-butyllithium; thionyl chloride; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

Reference yield:

: allyl-5,6-di-O-benzyl-2,3-di-O-isopropylidene-α-D-mannofuranoside

: 1015075-57-6
benzyl 2-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal

Guidance literature:: Multi-step reaction with 4 steps

1.1: palladium on activated charcoal / methanol / 10 h / Reflux

1.2: 0.5 h / 0 °C

2.1: sodium tetrahydroborate / ethanol / 10 h

3.1: thionyl chloride; triethylamine / dichloromethane / 0.5 h / -15 °C

3.2: 0.33 h

4.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h

4.2: 2 h / 20 °C

With sodium tetrahydroborate; n-butyllithium; thionyl chloride; palladium on activated charcoal; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane;