4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

Base Information

Chemical Name:4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside
CAS No.:309758-72-3
Molecular Formula:C₁₈H₂₀ClFO₇S
Molecular Weight:434.87
Hs Code.:

Synonyms:4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

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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 4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

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Technology Process of 4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

There total 1 articles about 4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-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: 67.0%

: 31077-89-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose

: 106-54-7
p-Chlorothiophenol

: 309758-72-3
4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 72h;
DOI:10.1021/ol006529i

Reference yield: 100.0%

: 309758-72-3
4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

: 309758-74-5
4-chlorophenyl 2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

Guidance literature:: With sodium methylate; In methanol; at 20 ℃;
DOI:10.1021/ol006529i

Reference yield:

: 309758-72-3
4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

: 309758-91-6
4-chlorophenyl (3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-(3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / NaOMe / methanol / 20 °C

2: 75 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 20 °C

3: 72 percent / NaH / tetrahydrofuran / 2 h / 60 °C

4: 80 percent / NaBH₃CN / tetrahydrofuran / 20 °C

5: 90 percent / pyridine / 20 °C

6: diphenylchlorosulfonium chloride / CH₂Cl₂ / 1.5 h / 20 °C

7: silver trifluoromethanesulfonate; 2,6-di-tert-butylpyridine / CH₂Cl₂; toluene / 1 h / 20 °C

8: 93 percent / NaOMe / CH₂Cl₂; methanol / 6 h / 20 °C

9: 115 mg / silver trifluoromethanesulfonate; 2,6-di-tert-butylpyridine / acetonitrile; toluene

10: 97 percent / NaOMe / CH₂Cl₂; methanol / 6 h / 20 °C

With pyridine; 2,6-di-tert-butyl-pyridine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; diphenylchlorosulfonium chloride; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 1: Deacetylation / 2: Substitution / 3: Etherification / 4: Reduction / 5: Acetylation / 6: Substitution / 7: Substitution / 8: Deacetylation / 9: Substitution / 10: Deacetylation;
DOI:10.1021/ol006529i