(5S,6R,9R)-3-Benzyloxy-6-[(E)-7-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-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)-7-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one
CAS No.:144446-45-7
Molecular Formula:C₄₉H₆₈O₇Si₂
Molecular Weight:825.246
Hs Code.:

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

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

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

There total 15 articles about (5S,6R,9R)-3-Benzyloxy-6-[(E)-7-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-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: 98.0%

: 107-30-2
chloromethyl methyl ether

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

: 144446-45-7
(5S,6R,9R)-3-Benzyloxy-6-[(E)-7-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-9-methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

Guidance literature:: With HNMPA; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 4h;
DOI:10.1021/jo980379w

Reference yield:

: 129144-88-3
2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2(E)-butenal

: 144446-45-7
(5S,6R,9R)-3-Benzyloxy-6-[(E)-7-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-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: 81 percent / PPh₃ / CH₂Cl₂ / 0 - 20 °C

2: Pd(PPh₃)4 / tetrahydrofuran; H₂O / 0.33 h

3: 90 percent / Et₃N / CH₂Cl₂ / 2 h

4: 95 percent / n-BuLi / tetrahydrofuran; hexane / 0.17 h / -100 °C

5: 72 percent / BHT / trichloroethene / 110 - 120 °C

6: 85 percent / K₂CO₃ / tetrahydrofuran / 6 h

7: 89 percent / DCC, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

8: 70 percent / LiH(TMS)2 / tetrahydrofuran; hexane / 1.) -78 deg C, 2 h, 2.) -78 deg C to room temperature, 1 h

9: 98 percent / i-Pr₂NEt, HNMPA / CH₂Cl₂ / 4 h / 0 °C

With dmap; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; HNMPA; LiH(TMS)2; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; Trichloroethylene; water;
DOI:10.1021/jo980379w

Reference yield:

: 144446-52-6
tert-Butyl-[(Z)-2-(2,2-dibromo-vinyl)-but-2-enyloxy]-diphenyl-silane

: 144446-45-7
(5S,6R,9R)-3-Benzyloxy-6-[(E)-7-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-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: Pd(PPh₃)4 / tetrahydrofuran; H₂O / 0.33 h

2: 90 percent / Et₃N / CH₂Cl₂ / 2 h

3: 95 percent / n-BuLi / tetrahydrofuran; hexane / 0.17 h / -100 °C

4: 72 percent / BHT / trichloroethene / 110 - 120 °C

5: 85 percent / K₂CO₃ / tetrahydrofuran / 6 h

6: 89 percent / DCC, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

7: 70 percent / LiH(TMS)2 / tetrahydrofuran; hexane / 1.) -78 deg C, 2 h, 2.) -78 deg C to room temperature, 1 h

8: 98 percent / i-Pr₂NEt, HNMPA / CH₂Cl₂ / 4 h / 0 °C

With dmap; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; HNMPA; LiH(TMS)2; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; Trichloroethylene; water;
DOI:10.1021/jo980379w