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-1-thio-β-D-glucopyranoside

Base Information

Chemical Name: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-1-thio-β-D-glucopyranoside
CAS No.:309758-87-0
Molecular Formula:C₄₆H₄₇ClF₂O₈S
Molecular Weight:833.39
Hs Code.:

Synonyms: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-1-thio-β-D-glucopyranoside

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Chemical Property of 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-1-thio-β-D-glucopyranoside

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Technology Process of 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-1-thio-β-D-glucopyranoside

There total 19 articles about 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-1-thio-β-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: 93.0%

: 309758-86-9
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-1-thio-β-D-glucopyranoside

: 309758-87-0
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-1-thio-β-D-glucopyranoside

Guidance literature:: With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 6h;
DOI:10.1021/ol006529i

Reference yield:

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

: 309758-87-0
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-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 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

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;
DOI:10.1021/ol006529i

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 309758-87-0
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-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 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

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;
DOI:10.1021/ol006529i