ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside

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Chemical Name:ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside
CAS No.:260970-06-7
Molecular Formula:C₂₂H₂₅FO₄S
Molecular Weight:404.503
Hs Code.:

Synonyms:ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside

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Chemical Property of ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside

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Technology Process of ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside

There total 11 articles about ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside 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: 99.0%

: 98-88-4
benzoyl chloride

: 260970-05-6
ethyl 3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside

: 260970-06-7
ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside

Guidance literature:: With pyridine; dmap; at 20 ℃; for 2.5h;
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

: 260970-06-7
ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 10 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

7.1: 97 percent / NaOMe / methanol / 1.5 h / Heating

8.1: oxalyl chloride; Me₂SO; Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: NaBH₄ / CH₂Cl₂; propan-2-ol / 0 - 20 °C

10.1: 99 percent / pyridine; DMAP / 2.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; diethylamino-sulfur trifluoride; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 1.1: Deacetylation / 2.1: Alkylation / 3.1: Acylation / 4.1: Hydrolysis / 5.1: stannylation / 5.2: Alkylation / 6.1: Fluorination / 7.1: debenzoylation / 8.1: Swern oxidation / 9.1: Reduction / 10.1: Acylation;
DOI:10.1016/S0008-6215(99)00203-7

Reference yield:

: 132799-10-1
ethyl 1-thio-α-L-fucopyranoside

: 260970-06-7
ethyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-1-thio-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: pyridine / 0 - 20 °C

3.1: 80 percent AcOH / 3.5 h / 50 °C

4.1: Bu₂SnO / toluene / 2 h / Heating

4.2: CsF / dimethylformamide / 40 °C

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

6.1: 97 percent / NaOMe / methanol / 1.5 h / Heating

7.1: oxalyl chloride; Me₂SO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: NaBH₄ / CH₂Cl₂; propan-2-ol / 0 - 20 °C

9.1: 99 percent / pyridine; DMAP / 2.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; diethylamino-sulfur trifluoride; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 1.1: Alkylation / 2.1: Acylation / 3.1: Hydrolysis / 4.1: stannylation / 4.2: Alkylation / 5.1: Fluorination / 6.1: debenzoylation / 7.1: Swern oxidation / 8.1: Reduction / 9.1: Acylation;
DOI:10.1016/S0008-6215(99)00203-7