(2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate

Base Information

• Chemical Name: (2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate
• CAS No.: 1255790-55-6
• Molecular Formula: C₅₆H₆₄N₂O₁₂
• Molecular Weight: 957.13

Synonyms:(2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate

Chemical Property of (2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate

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Technology Process of (2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate

There total 10 articles about (2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate 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: 80.0%

(4S,5S,6S)-4-benzyloxycarbonylamino-4,6-dimethyltetrahydro-2H-pyran-2,5-diyl acetate (1255790-61-4) + 8'-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-1'-((E)-but-2''-en-2''-yl)-11'-hydroxy-7',12'-dimethoxy-5'-methyl-4H-naphtho[2,3-h]chromen-4'-one (1255790-51-2) → (2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate (1255790-55-6)

Guidance literature:

With calcium sulfate; scandium tris(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at -30 - 0 ℃;

DOI:10.1021/ja107926f

Reference yield:

(E)-1''-(5'-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9',10'-dimethoxy-1'-methoxymethoxy-3'-methyl-8'-(triisopropylsilyloxy)anthracen-2'-yl)-4''-methylhex-4''-en-2''-yn-1''-one (1255790-48-7) → (2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate (1255790-55-6)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanol / 3 h / 20 °C / Inert atmosphere

2: lithium tetrafluoroborate; water / acetonitrile / 0.25 h / 82 °C / Inert atmosphere; Microwave irradiation

3: calcium sulfate; scandium tris(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 67.5 h / -30 - 0 °C / Inert atmosphere

With calcium sulfate; lithium tetrafluoroborate; water; scandium tris(trifluoromethanesulfonate); In ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/j.tet.2011.05.117

Reference yield:

(2R,4R,5S,6R)-5-benzyloxy-2-(6-benzyloxy-5,10-dimethoxy-8-methyl-4-(triisopropylsilyloxy)anthracen-1-yl)-N,N,6-trimethyltetrahydro-2H-pyran-4-amine (1273031-50-7) → (2S,3S,4S,6S)-6-(8-((2R,4R,5S,6R)-5-(benzyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)-2-((E)-but-2-en-2-yl)-11-hydroxy-7,12-dimethoxy-5-methyl-4-oxo-4H-naphtho[2,3-h]chromen-10-yl)-4-(((benzyloxy)carbonyl)amino)-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate (1255790-55-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine; 20% palladium hydroxide on carbon; hydrogen / methanol; ethyl acetate / 2 h

2.1: N-Bromosuccinimide / dichloromethane / 4 h / -78 - 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.42 h / 0 - 20 °C / Inert atmosphere

4.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

4.3: 20 °C / Inert atmosphere

5.1: barium manganate / benzene / 3.5 h / 20 °C / Inert atmosphere

6.1: ethanol / 3 h / 20 °C / Inert atmosphere

7.1: lithium tetrafluoroborate; water / acetonitrile / 0.25 h / 82 °C / Inert atmosphere; Microwave irradiation

8.1: calcium sulfate; scandium tris(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 67.5 h / -30 - 0 °C / Inert atmosphere

With pyridine; calcium sulfate; N-Bromosuccinimide; lithium tetrafluoroborate; barium manganate; 20% palladium hydroxide on carbon; water; hydrogen; tert.-butyl lithium; sodium hydride; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; acetonitrile; mineral oil; pentane; benzene;

DOI:10.1016/j.tet.2011.05.117

upstream raw materials:

(4S,5S,6S)-4-benzyloxycarbonylamino-4,6-dimethyltetrahydro-2H-pyran-2,5-diyl acetate

8'-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-1'-((E)-but-2''-en-2''-yl)-11'-hydroxy-7',12'-dimethoxy-5'-methyl-4H-naphtho[2,3-h]chromen-4'-one

(E)-1''-(5'-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-9',10'-dimethoxy-1'-methoxymethoxy-3'-methyl-8'-(triisopropylsilyloxy)anthracen-2'-yl)-4''-methylhex-4''-en-2''-yn-1''-one

8-benzyloxy-4-((2R,4R,5S,6R)-5-benzyloxytetrahydro-6-methyl-4-dimethylamino-2H-pyran-2-yl)-9,10-dimethoxy-6-methylanthracen-1-ol

Downstream raw materials:

10'-((2''S,3''S,4''S,6''S)-3''-acetoxy-4''-benzyloxycarbonylamino-2'',4''-dimethyltetrahydro-2H-pyran-6''-yl)-8'-((2R,4R,5S,6R)-5-benzyloxy-4-dimethylamino-6-methyltetrahydro-2H-pyran-2-yl)-1'-((E)-but-2'''-3n-2'''-yl)-7',12'-dimethoxy-5'-methyl-4'-oxo-4H-naphtho[2,3-h]chromen-11'-yl acetate

C₅₁H₆₀N₂O₁₃

C₄₇H₅₄N₂O₁₀

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