(12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one

Base Information

Chemical Name:(12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one
CAS No.:398478-33-6
Molecular Formula:C₃₃H₄₂O₇Si
Molecular Weight:578.778
Hs Code.:

(12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one

Synonyms:(12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one

There total 25 articles about (12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-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: 85.0%

: 398478-72-3
(12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

: 398478-33-6
(12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one

Guidance literature:: With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1021/ja0177713

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 398478-33-6
(12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

2: 84 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

3: 78 percent / pyridine / CH₂Cl₂ / 1.33 h / 0 °C

4: 85 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 20 °C

With morpholine; pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0177713

Reference yield:

: 164014-40-8
2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

: 398478-33-6
(12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 1.3 g / LiCl; Pd₂(dba)3; tri-(2-furyl)phosphine / 1-methyl-pyrrolidin-2-one / 48 h / 20 °C

2.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C

2.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C

3.1: 98 percent / K₂CO₃ / acetone / 40 h / 20 °C

4.1: 96 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 1 h / 20 °C

5.1: 88 percent / DEAD; PPh₃ / diethyl ether / 4 h / Heating

6.1: 8 percent / Cl₂[(Cy)3P]2Ru=CHPh / CH₂Cl₂ / 4 h / 20 °C

7.1: 96 percent / DDQ; H₂O / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

9.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C

10.1: 81 percent / BBr₃ / CH₂Cl₂ / 0.33 h / -78 °C

11.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

12.1: 84 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

13.1: 78 percent / pyridine / CH₂Cl₂ / 1.33 h / 0 °C

14.1: 85 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 20 °C

With morpholine; pyridine; 1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; ethylmagnesium bromide; tetrabutyl ammonium fluoride; water; boron tribromide; sodium hydride; potassium carbonate; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; diethylazodicarboxylate; Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; 5.1: Mitsunobu esterification / 8.1: Dess-Martin oxidation / 9.1: Horner-Wadsworth-Emmons homologation;
DOI:10.1021/ja0177713