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

Base Information

• Chemical Name: methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-3-O-tetrahydropyran-2-yl-α-L-talopyranoside
• CAS No.: 211993-03-2
• Molecular Formula: C₁₉H₂₇FO₅
• Molecular Weight: 354.419
• Mol file: 211993-03-2.mol

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

Chemical Property of methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-3-O-tetrahydropyran-2-yl-α-L-talopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-3-O-tetrahydropyran-2-yl-α-L-talopyranoside

There total 1 articles about methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-3-O-tetrahydropyran-2-yl-α-L-talopyranoside 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: 81.0%

3,4-dihydro-2H-pyran (110-87-2) + methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-α-L-talopyranoside (103946-10-7) → methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-3-O-tetrahydropyran-2-yl-α-L-talopyranoside (211993-03-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 5h; Ambient temperature;

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) → (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 (211992-93-7)

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

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:

3,4-dihydro-2H-pyran

methyl 4-O-benzyl-2,6-dideoxy-2-fluoro-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

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