ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-glucopyranoside

Base Information

Chemical Name:ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-glucopyranoside
CAS No.:260970-02-3
Molecular Formula:C₂₂H₂₅FO₄S
Molecular Weight:404.503
Hs Code.:

Synonyms:ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-glucopyranoside

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Chemical Property of ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-glucopyranoside

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Technology Process of ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-glucopyranoside

There total 7 articles about ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-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: 37.0%

: Benzoic acid (2R,3S,4S,5R,6S)-4-benzyloxy-2-ethylsulfanyl-6-methyl-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

: Benzoic acid (2R,3S,4R)-4-benzyloxy-2-ethylsulfanyl-6-methyl-3,4-dihydro-2H-pyran-3-yl ester

: Benzoic acid (2R,3S,6S)-4-benzyloxy-2-ethylsulfanyl-6-methyl-3,6-dihydro-2H-pyran-3-yl ester

: 260970-02-3
ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-glucopyranoside

Guidance literature:: With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 40 ℃;
DOI:10.1016/S0008-6215(99)00203-7

Reference yield:

: 260970-01-2
ethyl 2-O-benzoyl-3-O-benzyl-1-thio-β-L-fucopyranoside

: Benzoic acid (2R,3S,6S)-4-benzyloxy-2-ethylsulfanyl-6-methyl-3,6-dihydro-2H-pyran-3-yl ester

: 260970-02-3
ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-glucopyranoside

Guidance literature:: With diethylamino-sulfur trifluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0008-6215(99)00203-7

Reference yield:

: 127501-41-1
ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside

: 260970-02-3
ethyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-fluoro-1-thio-β-L-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaOMe / methanol / 0.75 h

2.1: p-toluenesulfonic acid hydrate / dimethylformamide / 2.5 h

3.1: pyridine / 0 - 20 °C

4.1: 80 percent AcOH / 3.5 h / 50 °C

5.1: Bu₂SnO / toluene / 2 h / Heating

5.2: CsF / dimethylformamide / 40 °C

6.1: diethylaminosulfur trifluoride (DAST) / tetrahydrofuran / 20 °C

With pyridine; diethylamino-sulfur trifluoride; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 1.1: Deacetylation / 2.1: Alkylation / 3.1: Acylation / 4.1: Hydrolysis / 5.1: stannylation / 5.2: Alkylation / 6.1: Fluorination;
DOI:10.1016/S0008-6215(99)00203-7