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

Base Information

• Chemical Name: 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
• CAS No.: 211993-30-5
• Molecular Formula: C₃₀H₃₁FO₁₂
• Molecular Weight: 602.567
• Mol file: 211993-30-5.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 50.0%

(+)-Daunomycinone (21794-55-8) + 3-O-acetyl-2,6-dideoxy-2-fluoro-4-O-methyl-α-L-talopyranosyl bromide (211993-07-6) → 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 (211993-30-5)

Guidance literature:

With 3 A molecular sieve; mercury dibromide; mercury(II) oxide; In dichloromethane; for 19h; Heating;

DOI:10.1016/S0008-6215(98)00026-3

Reference yield:

methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-α-L-talopyranoside (103946-10-7) → 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 (211993-30-5)

Guidance literature:

Multi-step reaction with 6 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

With 3 A molecular sieve; sulfuric acid; hydrogen; pyridinium p-toluenesulfonate; titanium(IV) bromide; sodium hydride; mercury dibromide; mercury(II) oxide; palladium; In 1,4-dioxane; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00026-3

Reference yield:

methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-3-O-tetrahydropyran-2-yl-α-L-talopyranoside (211993-03-2) → 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 (211993-30-5)

Guidance literature:

Multi-step reaction with 5 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

With 3 A molecular sieve; sulfuric acid; hydrogen; titanium(IV) bromide; sodium hydride; mercury dibromide; mercury(II) oxide; palladium; In 1,4-dioxane; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00026-3

upstream raw materials:

(+)-Daunomycinone

3-O-acetyl-2,6-dideoxy-2-fluoro-4-O-methyl-α-L-talopyranosyl bromide

methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-α-L-talopyranoside

methyl 2,6-dideoxy-2-fluoro-3-O-tetrahydropyran-2-yl-α-L-talopyranoside

Downstream raw materials:

(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