phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside

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Chemical Name:phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside
CAS No.:261374-37-2
Molecular Formula:C₂₀H₃₄O₄SSi
Molecular Weight:398.639
Hs Code.:

Synonyms:phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside

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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 phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside

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Technology Process of phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside

There total 6 articles about phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside 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: 77.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 261374-35-0
phenyl 2,3-di-O-methyl-1-thio-β-L-fucopyranoside

: 261374-37-2
phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 80 ℃; for 14h;
DOI:10.1021/ja993487o

Reference yield:

: 167612-34-2
phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside

: 261374-37-2
phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / KOH / methanol / 5 h

2.1: 83 percent / ZnCl₂; H₃PO₄ / 10 h

3.1: NaH / dimethylformamide / 1.5 h / 0 - 20 °C

4.1: 99 percent / 50percent aq. AcOH / 2 h / 100 °C

5.1: di-n-butyltin oxide / methanol / 2 h / Heating

5.2: 99 percent / CsF / dimethylformamide / 12 h

6.1: 77 percent / DMAP; imidazole / dimethylformamide / 14 h / 80 °C

With 1H-imidazole; dmap; potassium hydroxide; phosphoric acid; sodium hydride; di(n-butyl)tin oxide; zinc(II) chloride; In methanol; N,N-dimethyl-formamide; 1.1: Deacetylation / 2.1: cyclocondensation / 3.1: Methylation / 4.1: Hydrolysis / 5.1: Metallation / 5.2: Methylation / 6.1: silylation;
DOI:10.1021/ja993487o

Reference yield:

: 187233-24-5
phenyl 6-deoxy-1-thio-β-L-galactopyranoside

: 261374-37-2
phenyl 4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-1-thio-β-L-fucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / ZnCl₂; H₃PO₄ / 10 h

2.1: NaH / dimethylformamide / 1.5 h / 0 - 20 °C

3.1: 99 percent / 50percent aq. AcOH / 2 h / 100 °C

4.1: di-n-butyltin oxide / methanol / 2 h / Heating

4.2: 99 percent / CsF / dimethylformamide / 12 h

5.1: 77 percent / DMAP; imidazole / dimethylformamide / 14 h / 80 °C

With 1H-imidazole; dmap; phosphoric acid; sodium hydride; di(n-butyl)tin oxide; zinc(II) chloride; In methanol; N,N-dimethyl-formamide; 1.1: cyclocondensation / 2.1: Methylation / 3.1: Hydrolysis / 4.1: Metallation / 4.2: Methylation / 5.1: silylation;
DOI:10.1021/ja993487o