(4-O-acetyl-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-α-D-glucopyranosyl chloride

Base Information

• Chemical Name: (4-O-acetyl-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-α-D-glucopyranosyl chloride
• CAS No.: 309758-90-5
• Molecular Formula: C₆₂H₆₆ClF₃O₁₃
• Molecular Weight: 1111.65

Synonyms:(4-O-acetyl-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-α-D-glucopyranosyl chloride

Chemical Property of (4-O-acetyl-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-α-D-glucopyranosyl chloride

Chemical Property:

Purity/Quality:

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Technology Process of (4-O-acetyl-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-α-D-glucopyranosyl chloride

There total 19 articles about (4-O-acetyl-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-α-D-glucopyranosyl chloride 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: 81.0%

4-chlorophenyl (4-O-acetyl-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 (309758-89-2) → (4-O-acetyl-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-α-D-glucopyranosyl chloride (309758-90-5)

Guidance literature:

With diphenylchlorosulfonium chloride; In dichloromethane; for 1.5h;

DOI:10.1021/ol006529i

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose (31077-89-1) → (4-O-acetyl-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-α-D-glucopyranosyl chloride (309758-90-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 15 percent / BF₃*Et₂O / CH₂Cl₂ / 240 h / 20 °C

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

3: 76 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 3 h / 20 °C

4: 95 percent / NaH / dimethylformamide / 1 h / 20 °C

5: 95 percent / NaBH₃CN / tetrahydrofuran / 20 °C

6: 92 percent / pyridine / 20 °C

7: 91 percent / diphenylchlorosulfonium chloride / CH₂Cl₂ / 1.5 h / 20 °C

8: 26 percent / silver trifluoromethanesulfonate; 2,6-di-tert-butylpyridine / CH₂Cl₂; toluene / 1 h / 20 °C

9: 93 percent / NaOMe / CH₂Cl₂; methanol / 6 h / 20 °C

10: 115 mg / silver trifluoromethanesulfonate; 2,6-di-tert-butylpyridine / acetonitrile; toluene

11: 81 percent / diphenylchlorosulfonium chloride / CH₂Cl₂ / 1.5 h

With pyridine; 2,6-di-tert-butyl-pyridine; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; diphenylchlorosulfonium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Substitution / 2: Deacetylation / 3: Substitution / 4: Etherification / 5: Reduction / 6: Acetylation / 7: Substitution / 8: Substitution / 9: Deacetylation / 10: Substitution / 11: Substitution;

DOI:10.1021/ol006529i

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (4-O-acetyl-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-α-D-glucopyranosyl chloride (309758-90-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 76 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 3 h / 20 °C

2: 95 percent / NaH / dimethylformamide / 1 h / 20 °C

3: 95 percent / NaBH₃CN / tetrahydrofuran / 20 °C

4: 92 percent / pyridine / 20 °C

5: 91 percent / diphenylchlorosulfonium chloride / CH₂Cl₂ / 1.5 h / 20 °C

6: 26 percent / silver trifluoromethanesulfonate; 2,6-di-tert-butylpyridine / CH₂Cl₂; toluene / 1 h / 20 °C

7: 93 percent / NaOMe / CH₂Cl₂; methanol / 6 h / 20 °C

8: 115 mg / silver trifluoromethanesulfonate; 2,6-di-tert-butylpyridine / acetonitrile; toluene

9: 81 percent / diphenylchlorosulfonium chloride / CH₂Cl₂ / 1.5 h

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; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Substitution / 2: Etherification / 3: Reduction / 4: Acetylation / 5: Substitution / 6: Substitution / 7: Deacetylation / 8: Substitution / 9: Substitution;

DOI:10.1021/ol006529i

upstream raw materials:

4-chlorophenyl (4-O-acetyl-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

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

benzaldehyde dimethyl acetal

4-chlorophenyl 2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside

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