(1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

Base Information

Chemical Name:(1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde
CAS No.:773104-57-7
Molecular Formula:C₃₅H₅₂O₈Si
Molecular Weight:628.879
Hs Code.:

(1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

Synonyms:(1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

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Chemical Property of (1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

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Technology Process of (1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

There total 14 articles about (1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde 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: 81.0%

: 773104-58-8
(2E,5R,6S,7Z,9E,12R)-12-(tert-butyldimethylsilyloxy)-13-[(6R)-4-methoxymethoxy-5,6-dihydropyran-2-one-6-yl]-6-[(4-methoxyphenyl)methoxy]-5-methyl-2,7,9-tridecatrienal

: (R)-6-{(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[(6R,7S)-7-(4-methoxy-benzyloxy)-6-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-1-yl]-pent-4-enyl}-4-methoxymethoxy-5,6-dihydro-pyran-2-one

: 773104-57-7
(1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

: (1S,2R,3aR,4R,5R,7aR)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

Guidance literature:: With 2,6-di-tert-butyl-4-methyl-phenol; In toluene; at 150 ℃; for 9h;
DOI:10.1021/ja048320w

Reference yield:

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

: 773104-57-7
(1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

Guidance literature:: Multi-step reaction with 14 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: aq. Zn(NO₃)2; K₂CO₃ / methanol / 105 h / 0 °C

8.1: 143 mg / Et₃N / CH₂Cl₂ / 0.5 h / -18 °C

9.1: 89 percent / imidazole / dimethylformamide / 11 h / 0 °C

10.1: Bu₃SnH; azobisisobutyronitrile / benzene / 46 h / Heating

10.2: 697 mg / I₂ / CH₂Cl₂ / 0.5 h / 0 °C

11.1: CuCl; PdCl₂(MeCN)2 / dimethylsulfoxide / 10 h

12.1: 356 mg / HF*pyridine / tetrahydrofuran / 12 h / 0 °C

13.1: 94 percent / MnO₂ / CH₂Cl₂ / 0.5 h / 0 °C

14.1: 81 percent / 2,6-di-tert-butyl-4-methylphenol / toluene / 9 h / 150 °C

With 1H-imidazole; manganese(IV) oxide; dichloro bis(acetonitrile) palladium(II); zinc(II) nitrate; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); 2,6-di-tert-butyl-4-methyl-phenol; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 3.1: Mukaiyama aldol reaction / 4.1: Dess-Martin oxidation / 6.1: Prasad's procedure / 11.1: Stille coupling / 14.1: intramolecular Diels-Alder reaction;
DOI:10.1021/ja048320w

Reference yield:

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

: 773104-57-7
(1S,2R,3aS,4S,5S,7aS)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-4-methoxymethoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl]-1-(4-methoxy-benzyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

Guidance literature:: Multi-step reaction with 13 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: aq. Zn(NO₃)2; K₂CO₃ / methanol / 105 h / 0 °C

7.1: 143 mg / Et₃N / CH₂Cl₂ / 0.5 h / -18 °C

8.1: 89 percent / imidazole / dimethylformamide / 11 h / 0 °C

9.1: Bu₃SnH; azobisisobutyronitrile / benzene / 46 h / Heating

9.2: 697 mg / I₂ / CH₂Cl₂ / 0.5 h / 0 °C

10.1: CuCl; PdCl₂(MeCN)2 / dimethylsulfoxide / 10 h

11.1: 356 mg / HF*pyridine / tetrahydrofuran / 12 h / 0 °C

12.1: 94 percent / MnO₂ / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 81 percent / 2,6-di-tert-butyl-4-methylphenol / toluene / 9 h / 150 °C

With 1H-imidazole; manganese(IV) oxide; dichloro bis(acetonitrile) palladium(II); zinc(II) nitrate; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); 2,6-di-tert-butyl-4-methyl-phenol; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 2.1: Mukaiyama aldol reaction / 3.1: Dess-Martin oxidation / 5.1: Prasad's procedure / 10.1: Stille coupling / 13.1: intramolecular Diels-Alder reaction;
DOI:10.1021/ja048320w