(Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

Base Information

Chemical Name:(Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester
CAS No.:773104-68-0
Molecular Formula:C₃₂H₄₄O₉
Molecular Weight:572.696
Hs Code.:

(Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

Synonyms:(Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

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Chemical Property of (Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

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Technology Process of (Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

There total 19 articles about (Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl 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: 29.0%

: 773104-67-9
(2Z,4E,7R,8S,9Z,11E,14R,16R)-2-methoxycarbonyl-14,16-di(methoxymethoxy)-8-[(4-methoxyphenyl)methoxy]-7-methyl-2,4,9,11-cycloheptadecatetraen-1-one

: 773104-68-0
(Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

Guidance literature:: With 2,6-di-tert-butyl-4-methyl-phenol; In toluene; at 130 ℃; for 80h;
DOI:10.1021/ja048320w

Reference yield:

: 182681-88-5
(2R)-1-cyano-2-hydroxy-4-pentyne

: 773104-68-0
(Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: 5.62 g / imidazole / dimethylformamide / 13.5 h / 0 °C

2.1: 100 percent / DIBAL-H / toluene / 2 h / -52 °C

3.1: BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 6.5 h / 0 °C

5.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C

6.1: 100 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 8 h / -78 °C

7.1: 93 percent / imidazole / dimethylformamide / 5 h / 0 °C

8.1: 97 percent / NBS; AgNO₃ / acetone / 0.5 h / 20 °C

9.1: Pd₂(dba)3; PPh₃; Bu₃SnH / tetrahydrofuran / 2 h

9.2: 84 percent / I₂ / CH₂Cl₂ / 1 h / 0 °C

10.1: 97 percent / CuCl; Pd(PPh₃)4 / dimethylsulfoxide; tetrahydrofuran / 2 h

11.1: 94 percent / NH₄F / methanol / 24 h / 0 °C

12.1: 100 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

13.1: 100 percent / HF*pyridine / 45 h / 0 °C

14.1: 94 percent / iPr₂NEt / CH₂Cl₂ / 41 h

15.1: 96 percent / toluene; methanol / 5 h / 110 °C

16.1: Pd(PPh₃)4; dppe / tetrahydrofuran / 3 h

17.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

17.2: 331 mg / tetrahydrofuran; toluene / 2 h / -78 °C

18.1: 140.3 mg / mCPBA / CH₂Cl₂ / 3 h / -78 °C

19.1: 29 percent / 2,6-di-tert-butyl-4-methylphenol / toluene / 80 h / 130 °C

With pyridine; 1H-imidazole; ammonium fluoride; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 2,6-di-tert-butyl-4-methyl-phenol; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; silver nitrate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,2-bis-(diphenylphosphino)ethane; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Mukaiyama aldol reaction / 4.1: Dess-Martin oxidation / 6.1: Prasad's procedure / 10.1: Stille coupling / 19.1: intramolecular Diels-Alder reaction;
DOI:10.1021/ja048320w

Reference yield:

: 640270-65-1
(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}hex-5-ynenitrile

: 773104-68-0
(Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: 100 percent / DIBAL-H / toluene / 2 h / -52 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 6.5 h / 0 °C

4.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C

5.1: 100 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 8 h / -78 °C

6.1: 93 percent / imidazole / dimethylformamide / 5 h / 0 °C

7.1: 97 percent / NBS; AgNO₃ / acetone / 0.5 h / 20 °C

8.1: Pd₂(dba)3; PPh₃; Bu₃SnH / tetrahydrofuran / 2 h

8.2: 84 percent / I₂ / CH₂Cl₂ / 1 h / 0 °C

9.1: 97 percent / CuCl; Pd(PPh₃)4 / dimethylsulfoxide; tetrahydrofuran / 2 h

10.1: 94 percent / NH₄F / methanol / 24 h / 0 °C

11.1: 100 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

12.1: 100 percent / HF*pyridine / 45 h / 0 °C

13.1: 94 percent / iPr₂NEt / CH₂Cl₂ / 41 h

14.1: 96 percent / toluene; methanol / 5 h / 110 °C

15.1: Pd(PPh₃)4; dppe / tetrahydrofuran / 3 h

16.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

16.2: 331 mg / tetrahydrofuran; toluene / 2 h / -78 °C

17.1: 140.3 mg / mCPBA / CH₂Cl₂ / 3 h / -78 °C

18.1: 29 percent / 2,6-di-tert-butyl-4-methylphenol / toluene / 80 h / 130 °C

With pyridine; 1H-imidazole; ammonium fluoride; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 2,6-di-tert-butyl-4-methyl-phenol; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; silver nitrate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1,2-bis-(diphenylphosphino)ethane; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 2.1: Mukaiyama aldol reaction / 3.1: Dess-Martin oxidation / 5.1: Prasad's procedure / 9.1: Stille coupling / 18.1: intramolecular Diels-Alder reaction;
DOI:10.1021/ja048320w