(diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

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Chemical Name:(diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester
CAS No.:477200-99-0
Molecular Formula:C₆₁H₉₄IO₉PSSi₂
Molecular Weight:1217.53
Hs Code.:

(diethoxy-phosphoryl)-acetic acid 8-{4-[2-(<i>tert</i>-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Synonyms:(diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

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Chemical Property of (diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

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Technology Process of (diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

There total 30 articles about (diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester 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: 78.0%

: 34170-81-5
diethyl (2-chloro-2-oxoethyl)phosphonate

: 477200-98-9
(1E,8E,10E)-(3R,4S,5S,7S,12R)-12-{(2R,4R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-iodo-3-methoxy-2,4,8-trimethyl-7-triisopropylsilanyloxy-trideca-1,8,10-trien-5-ol

: 477200-99-0
(diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/jo020537q

Reference yield:

: 112897-05-9
(5R,4R)-6-tert-butyldimethylsilyloxy-4-hydroxy-5-methylhex-1-ene

: 477200-99-0
(diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 92 percent / N-iodosuccinimide / CH₂Cl₂ / 15 h / -23 - 0 °C

2.1: 97 percent / OsO₄; sodium periodate / tetrahydrofuran; H₂O; propan-2-ol / 15 h

3.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.67 h / -78 °C

3.2: 65 percent / tetrahydrofuran; toluene / 0.92 h / -78 °C

4.1: 86 percent / tri-n-butylstannane; azobisisobutyronitrile / toluene / 2 h / 80 °C

5.1: 87 percent / MgBr₂*OEt₂ / diethyl ether / 2 h / 20 °C

6.1: 92 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 4 h / 0 - 20 °C

7.1: 76 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

8.1: 93 percent / acetic acid / tetrahydrofuran; H₂O / 18 h / 20 °C

9.1: 71 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - -20 °C

10.1: 77 percent / tetrahydrofuran / 16 °C / Heating

11.1: 92 percent / diisobutylaluminum hydride / diethyl ether; various solvent(s) / 1 h / -78 °C

12.1: 90 percent / manganese dioxide / diethyl ether / 2 h / 20 °C

13.1: diethyl ether / 3 h / -10 °C

13.2: 226 mg / H₂O₂ / diethyl ether; methanol; H₂O / 1.17 h / 0 - 20 °C / pH 7.0

14.1: 74 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile; tetrahydrofuran / -25 - -10 °C

15.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 3.83 h / -8 °C

16.1: 78 percent / pyridine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium tetrahydroborate; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; calcium chloride; magnesium bromide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetic acid; isopropyl alcohol; toluene; acetonitrile; 3.2: Wadsworth-Emmons condensation / 10.1: Wittig reaction;
DOI:10.1021/jo020537q

Reference yield:

: 197771-06-5
tert-Butyl-[(2R,3R)-3-(1-ethoxy-2-iodo-ethoxy)-2-methyl-hex-5-enyloxy]-dimethyl-silane

: 477200-99-0
(diethoxy-phosphoryl)-acetic acid 8-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-2-yl}-1-(4-iodo-2-methoxy-1,3-dimethyl-but-3-enyl)-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 97 percent / OsO₄; sodium periodate / tetrahydrofuran; H₂O; propan-2-ol / 15 h

2.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.67 h / -78 °C

2.2: 65 percent / tetrahydrofuran; toluene / 0.92 h / -78 °C

3.1: 86 percent / tri-n-butylstannane; azobisisobutyronitrile / toluene / 2 h / 80 °C

4.1: 87 percent / MgBr₂*OEt₂ / diethyl ether / 2 h / 20 °C

5.1: 92 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / 4 h / 0 - 20 °C

6.1: 76 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

7.1: 93 percent / acetic acid / tetrahydrofuran; H₂O / 18 h / 20 °C

8.1: 71 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - -20 °C

9.1: 77 percent / tetrahydrofuran / 16 °C / Heating

10.1: 92 percent / diisobutylaluminum hydride / diethyl ether; various solvent(s) / 1 h / -78 °C

11.1: 90 percent / manganese dioxide / diethyl ether / 2 h / 20 °C

12.1: diethyl ether / 3 h / -10 °C

12.2: 226 mg / H₂O₂ / diethyl ether; methanol; H₂O / 1.17 h / 0 - 20 °C / pH 7.0

13.1: 74 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile; tetrahydrofuran / -25 - -10 °C

14.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 3.83 h / -8 °C

15.1: 78 percent / pyridine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; calcium chloride; magnesium bromide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetic acid; isopropyl alcohol; toluene; acetonitrile; 2.2: Wadsworth-Emmons condensation / 9.1: Wittig reaction;
DOI:10.1021/jo020537q