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

Base Information

Chemical Name:Acetic acid (2S,3R,4R,5R,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-methoxy-2-methyl-tetrahydro-pyran-3-yl ester
CAS No.:211993-28-1
Molecular Formula:C₃₀H₃₁FO₁₂
Molecular Weight:602.567
Hs Code.:

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

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

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

There total 5 articles about Acetic acid (2S,3R,4R,5R,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 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: 8.0%

: 21794-55-8
(+)-Daunomycinone

: 211993-02-1
4-O-acetyl-2,6-dideoxy-2-fluoro-3-O-methyl-α-L-talopyranosyl bromide

: 211993-28-1
Acetic acid (2S,3R,4R,5R,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

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

Guidance literature:: With 3 A molecular sieve; mercury dibromide; mercury(II) oxide; In dichloromethane; for 17h; Heating;
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

: 211993-28-1
Acetic acid (2S,3R,4R,5R,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / 60percent NaH in mineral oil / dimethylformamide / 1 h / Ambient temperature

2: H₂ / Pd black / acetic acid; dioxane; H₂O / 1 h / Ambient temperature

3: 78 percent / H₂SO₄ / nitromethane / 2.5 h / Ambient temperature

4: 88 percent / TiBr₄ / CH₂Cl₂; ethyl acetate / 16 h / Ambient temperature

5: 38 percent / yellow HgO, HgBr₂, molecular sieves 3A / CH₂Cl₂ / 17 h / Heating

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

Reference yield:

: 211992-98-2
methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-3-O-methyl-α-L-talopyranoside

: 211993-28-1
Acetic acid (2S,3R,4R,5R,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / Pd black / acetic acid; dioxane; H₂O / 1 h / Ambient temperature

2: 78 percent / H₂SO₄ / nitromethane / 2.5 h / Ambient temperature

3: 88 percent / TiBr₄ / CH₂Cl₂; ethyl acetate / 16 h / Ambient temperature

4: 38 percent / yellow HgO, HgBr₂, molecular sieves 3A / CH₂Cl₂ / 17 h / Heating

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