4-O-acetyl-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 chloride
CAS No.:309758-84-7
Molecular Formula:C₂₂H₂₄ClFO₅
Molecular Weight:422.881
Hs Code.:

Synonyms:4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl chloride

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Chemical Property of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl chloride

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Technology Process of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl chloride

There total 15 articles about 4-O-acetyl-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: 91.0%

: 309758-83-6
4-chlorophenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside

: 309758-84-7
4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl chloride

Guidance literature:: With diphenylchlorosulfonium chloride; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ol006529i

Reference yield:

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

: 309758-85-8
4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-β-D-glucopyranosyl chloride

: 309758-84-7
4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl chloride

Guidance literature:: With diphenylchlorosulfonium chloride; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ol006529i

Reference yield:

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

: 309758-84-7
4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl chloride

Guidance literature:: Multi-step reaction with 7 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

With pyridine; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; diphenylchlorosulfonium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Deacetylation / 3: Substitution / 4: Etherification / 5: Reduction / 6: Acetylation / 7: Substitution;
DOI:10.1021/ol006529i