(5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Base Information

Chemical Name:(5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one
CAS No.:144476-53-9
Molecular Formula:C₄₅H₆₀O₇Si₂
Molecular Weight:769.138
Hs Code.:

(5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

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Chemical Property of (5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

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Useful:

Technology Process of (5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

There total 10 articles about (5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one 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:

: 146983-23-5
4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2(E),4(Z)-hexadienal

: 144476-53-9
(5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / CH₂Cl₂ / 10 h / Heating

2: BHT / trichloroethene / 120 °C

3: 95 percent / DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

4: 89 percent / imidazole / dimethylformamide / 14 h / 23 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to room temperature

6: 99 percent / K₂CO₃ / 10 h / Ambient temperature

7: 92 percent / DCC, DMAP / CH₂Cl₂ / 16 h

8: LiN(TMS)2 / tetrahydrofuran; hexane / 1.) -78 deg C, 2 h, 2.) -78 deg C to room temperature, 45 min

9: i-Pr₂NEt / diethyl ether; hexamethylphosphoric acid triamide / 3 h / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; Trichloroethylene; N,N-dimethyl-formamide;
DOI:10.1021/jo980379w

Reference yield:

: 144446-46-8
(2E,4E,6Z)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-octa-2,4,6-trienoic acid methyl ester

: 144476-53-9
(5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: BHT / trichloroethene / 120 °C

2: 95 percent / DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

3: 89 percent / imidazole / dimethylformamide / 14 h / 23 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to room temperature

5: 99 percent / K₂CO₃ / 10 h / Ambient temperature

6: 92 percent / DCC, DMAP / CH₂Cl₂ / 16 h

7: LiN(TMS)2 / tetrahydrofuran; hexane / 1.) -78 deg C, 2 h, 2.) -78 deg C to room temperature, 45 min

8: i-Pr₂NEt / diethyl ether; hexamethylphosphoric acid triamide / 3 h / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; Trichloroethylene; N,N-dimethyl-formamide;
DOI:10.1021/jo980379w

Reference yield:

: 213182-14-0
(2R,5S,6R,9R)-2-tert-Butyl-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-1,3-dioxa-spiro[4.5]dec-7-en-4-ol

: 144476-53-9
(5S,6R,9R)-3-Benzyloxy-6-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to room temperature

2: 99 percent / K₂CO₃ / 10 h / Ambient temperature

3: 92 percent / DCC, DMAP / CH₂Cl₂ / 16 h

4: LiN(TMS)2 / tetrahydrofuran; hexane / 1.) -78 deg C, 2 h, 2.) -78 deg C to room temperature, 45 min

5: i-Pr₂NEt / diethyl ether; hexamethylphosphoric acid triamide / 3 h / 0 °C

With dmap; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo980379w