(8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

Base Information

Chemical Name:(8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione
CAS No.:211992-93-7
Molecular Formula:C₂₈H₂₉FO₁₁
Molecular Weight:560.53
Hs Code.:

(8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

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Chemical Property of (8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

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Technology Process of (8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

There total 7 articles about (8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione 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: 96.0%

: 211993-30-5
Acetic acid (2R,3R,4R,5R,6S)-2-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-fluoro-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

: 211992-93-7
(8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; for 1h;
DOI:10.1016/S0008-6215(98)00026-3

Reference yield:

: 103946-10-7
methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-α-L-talopyranoside

: 211992-93-7
(8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 81 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h / Ambient temperature

2: 83 percent / H₂ / Pd black / dioxane; H₂O / 2 h / Ambient temperature

3: 74 percent / 60percent NaH in mineral oil / dimethylformamide / 2 h / Ambient temperature

4: 64 percent / H₂SO₄ / acetic acid / 1 h, 0 deg C; 1,5 h, RT

5: TiBr₄ / CH₂Cl₂; ethyl acetate / 16 h / Ambient temperature

6: 50 percent / yellow HgO, HgBr₂, molecular sieves 3A / CH₂Cl₂ / 19 h / Heating

7: 96 percent / 1M aq NaOH / tetrahydrofuran / 1 h

With sodium hydroxide; 3 A molecular sieve; sulfuric acid; hydrogen; pyridinium p-toluenesulfonate; titanium(IV) bromide; sodium hydride; mercury dibromide; mercury(II) oxide; palladium; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(98)00026-3

Reference yield:

: 211993-03-2
methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-3-O-tetrahydropyran-2-yl-α-L-talopyranoside

: 211992-93-7
(8S,10S)-8-Acetyl-10-((2R,3R,4R,5S,6S)-3-fluoro-4-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / H₂ / Pd black / dioxane; H₂O / 2 h / Ambient temperature

2: 74 percent / 60percent NaH in mineral oil / dimethylformamide / 2 h / Ambient temperature

3: 64 percent / H₂SO₄ / acetic acid / 1 h, 0 deg C; 1,5 h, RT

4: TiBr₄ / CH₂Cl₂; ethyl acetate / 16 h / Ambient temperature

5: 50 percent / yellow HgO, HgBr₂, molecular sieves 3A / CH₂Cl₂ / 19 h / Heating

6: 96 percent / 1M aq NaOH / tetrahydrofuran / 1 h

With sodium hydroxide; 3 A molecular sieve; sulfuric acid; hydrogen; titanium(IV) bromide; sodium hydride; mercury dibromide; mercury(II) oxide; palladium; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(98)00026-3