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

Base Information

Chemical Name:4-chlorophenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside
CAS No.:309758-82-5
Molecular Formula:C₂₈H₂₈ClFO₅S
Molecular Weight:531.045
Hs Code.:

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

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Chemical Property of 4-chlorophenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

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

There total 8 articles about 4-chlorophenyl 4-O-acetyl-3,6-di-O-benzyl-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: 90.0%

: 108-24-7
acetic anhydride

: 309758-80-3
4-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

: 309758-82-5
4-chlorophenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

Guidance literature:: With pyridine; at 20 ℃;
DOI:10.1021/ol006529i

Reference yield:

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

: 309758-82-5
4-chlorophenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 67 percent / BF₃*Et₂O / CH₂Cl₂ / 72 h / 20 °C

2: 100 percent / NaOMe / methanol / 20 °C

3: 75 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 20 °C

4: 72 percent / NaH / tetrahydrofuran / 2 h / 60 °C

5: 80 percent / NaBH₃CN / tetrahydrofuran / 20 °C

6: 90 percent / pyridine / 20 °C

With pyridine; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: Substitution / 2: Deacetylation / 3: Substitution / 4: Etherification / 5: Reduction / 6: Acetylation;
DOI:10.1021/ol006529i

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 309758-82-5
4-chlorophenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 20 °C

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

3: 80 percent / NaBH₃CN / tetrahydrofuran / 20 °C

4: 90 percent / pyridine / 20 °C

With pyridine; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; acetonitrile; 1: Substitution / 2: Etherification / 3: Reduction / 4: Acetylation;
DOI:10.1021/ol006529i