methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

Base Information

Chemical Name:methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate
CAS No.:243866-40-2
Molecular Formula:C₃₂H₄₄O₉SSi
Molecular Weight:632.847
Hs Code.:

Synonyms:methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

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Chemical Property of methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

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Technology Process of methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

There total 5 articles about methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate 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: 93.0%

: 98-88-4
benzoyl chloride

: 243866-37-7
methyl (phenyl 4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

: 243866-40-2
methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

Guidance literature:: With pyridine; In dichloromethane; at -40 ℃; for 6h;
DOI:10.1080/07328309908544026

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 243866-40-2
methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 2 steps

1: 88 percent / imidazole / dimethylformamide / 4 h / 20 °C

2: 93 percent / pyridine / CH₂Cl₂ / 6 h / -40 °C

With pyridine; 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Acylation;
DOI:10.1080/07328309908544026

Reference yield:

: Methyl (phenyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

: 243866-40-2
methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / NaOMe / methanol / 2 h / 0 °C / pH 9.0

2: 92 percent / Dowex 50W-X₈ (H⁺ form) / acetone / 6 h / 20 °C

3: 88 percent / imidazole / dimethylformamide / 4 h / 20 °C

4: 93 percent / pyridine / CH₂Cl₂ / 6 h / -40 °C

With pyridine; 1H-imidazole; Dowex 50W-X₈ (H⁺ form); sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1: Deacetylation / 2: ketalization / 3: silylation / 4: Acylation;
DOI:10.1080/07328309908544026