(3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Base Information

Chemical Name:(3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one
CAS No.:127354-61-4
Molecular Formula:C₄₁H₆₇NO₄SSi₃
Molecular Weight:754.31
Hs Code.:

(3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Synonyms:(3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

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Chemical Property of (3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

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Technology Process of (3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

There total 1 articles about (3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-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%

: 90741-78-9,90741-79-0,116205-80-2
C₄₈H₇₁NO₅SSi₃

: 127354-61-4
(3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at -78 - 0 ℃; for 0.333333h; 1.) -78 deg C, 8 min, 2.) from -35 deg C to 30 deg C, 7 min, 3.) 0 deg C, 5 min;
DOI:10.1021/ja00167a036

Reference yield: 5.0%

: 127354-61-4
(3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

: 127354-62-5,127470-55-7
C₄₁H₆₉NO₄SSi₃

: 127354-62-5,127470-55-7
C₄₁H₆₉NO₄SSi₃

Guidance literature:: With diisobutylaluminium hydride; In hexane; toluene; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja00167a036

Reference yield:

: 127354-61-4
(3S,3aR,4S,7S,7aS)-3-Benzyl-7a-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-3,6-dihydro-2H-thiopyran-2-carbonyl]-7-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-4-methyl-5-trimethylsilanylmethyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

: 114634-53-6,127354-65-8
C₃₃H₄₃NO₅SSi

Guidance literature:: Multi-step reaction with 5 steps

1: 63 percent / diisobutylaluminum hydride (DIBAL) / toluene; hexane / 0.08 h / 0 °C

2: 87 percent / triethylamine, 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 312 h

3: 85 percent / HNEt₃F / tetrahydrofuran; methanol / 12 h / Ambient temperature

4: 92 percent / tri-n-butylphosphine, carbon tetrachloride / 0.08 h

5: 24 percent / NaI, K₂CO₃ / acetonitrile / 17 h / 68 - 70 °C

With tetrachloromethane; dmap; tributylphosphine; diisobutylaluminium hydride; potassium carbonate; triethylamine hydrofluoride; triethylamine; sodium iodide; In tetrahydrofuran; methanol; hexane; toluene; acetonitrile;
DOI:10.1021/ja00167a036