(16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole

Base Information

Chemical Name:(16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole
CAS No.:809285-62-9
Molecular Formula:C₆₀H₇₀N₂O₁₂
Molecular Weight:1011.22
Hs Code.:

Synonyms:(16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole

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Chemical Property of (16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole

Chemical Property:

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Technology Process of (16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole

There total 44 articles about (16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole 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: 79.0%

: 809285-87-8
C₆₀H₇₂N₂O₁₃

: 809285-62-9
(16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole

Guidance literature:: C₆₀H₇₂N₂O₁₃; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h;

With dmap; In tetrahydrofuran; toluene; at 20 ℃; for 12h;
DOI:10.1021/ja0443068

Reference yield:

: 286372-15-4
(3R)-3-methoxypent-4-ynoic acid

: 809285-62-9
(16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole

Guidance literature:: Multi-step reaction with 9 steps

1.1: 55 percent / 1-hydroxybenzotriazole; EDC; N-methylmorpholine / CH₂Cl₂ / 16 h / 20 °C

2.1: diethylaminosulfurtrifluoride / CH₂Cl₂ / 1 h / -78 °C

2.2: K₂CO₃ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

2.3: 106.3 mg / BrCCl₃; DBU / CH₂Cl₂ / 20 h / 4 °C

3.1: 54 percent / AgNO₃; N-bromosuccinimide / acetone / 1 h / 20 °C

4.1: PdCl₂(PPh₃)2; n-Bu₄SnH / tetrahydrofuran / 3.5 h / -78 - 0 °C

4.2: 92 percent / I₂ / tetrahydrofuran

5.1: 94 percent / PdCl₂(PPh₃)2; CuI; Et₃N / acetonitrile / cooling

6.1: 80 percent / DMAP; dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / 20 °C

7.1: 94 percent / PdCl₂(PPh₃)2; CuI / acetonitrile / 1.25 h

8.1: 98 percent / aq. LiOH / tetrahydrofuran / 13.5 h / 20 °C

9.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

9.2: 79 percent / DMAP / tetrahydrofuran; toluene / 12 h / 20 °C

With 4-methyl-morpholine; dmap; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; N-Bromosuccinimide; copper(l) iodide; diethylamino-sulfur trifluoride; n-Bu₄SnH; 2,4,6-trichlorobenzoyl chloride; benzotriazol-1-ol; silver nitrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; 5.1: Sonogashira cross-coupling / 6.1: Sonogashira coupling / 9.1: Yamaguchi lactonization;
DOI:10.1021/ja0443068

Reference yield:

: 809285-65-2
(3R)-5-(triisopropylsilyloxy)-1-(trimethylsilyl)pent-1-yn-3-ol

: 809285-62-9
(16,16’)-bis(4-methoxybenzyloxy)-(9,10,9’,10’)-tetradehydridodisorazole

Guidance literature:: Multi-step reaction with 11 steps

1.1: 95 percent / aq. NaOH; n-Bu₄NHSO₄ / toluene / 3.5 h / 0 - 20 °C

2.1: aq. HF / acetonitrile / 24 h / 20 °C

2.2: 99 percent / TEMPO; NaClO₂; NaOCl / aq. phosphate buffer; acetonitrile / 18 h / pH 6.7 / Heating

3.1: 55 percent / 1-hydroxybenzotriazole; EDC; N-methylmorpholine / CH₂Cl₂ / 16 h / 20 °C

4.1: diethylaminosulfurtrifluoride / CH₂Cl₂ / 1 h / -78 °C

4.2: K₂CO₃ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

4.3: 106.3 mg / BrCCl₃; DBU / CH₂Cl₂ / 20 h / 4 °C

5.1: 54 percent / AgNO₃; N-bromosuccinimide / acetone / 1 h / 20 °C

6.1: PdCl₂(PPh₃)2; n-Bu₄SnH / tetrahydrofuran / 3.5 h / -78 - 0 °C

6.2: 92 percent / I₂ / tetrahydrofuran

7.1: 94 percent / PdCl₂(PPh₃)2; CuI; Et₃N / acetonitrile / cooling

8.1: 80 percent / DMAP; dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / 20 °C

9.1: 94 percent / PdCl₂(PPh₃)2; CuI / acetonitrile / 1.25 h

10.1: 98 percent / aq. LiOH / tetrahydrofuran / 13.5 h / 20 °C

11.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

11.2: 79 percent / DMAP / tetrahydrofuran; toluene / 12 h / 20 °C

With 4-methyl-morpholine; dmap; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; copper(l) iodide; diethylamino-sulfur trifluoride; n-Bu₄SnH; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; silver nitrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone; toluene; acetonitrile; 7.1: Sonogashira cross-coupling / 8.1: Sonogashira coupling / 11.1: Yamaguchi lactonization;
DOI:10.1021/ja0443068