2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan

Base Information

Chemical Name:2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan
CAS No.:244058-02-4
Molecular Formula:C₄₁H₅₂O₆Si
Molecular Weight:668.946
Hs Code.:

Synonyms:2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan

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Chemical Property of 2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan

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Technology Process of 2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan

There total 6 articles about 2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan 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: 94.0%

: 108-24-7
acetic anhydride

: 244058-01-3
2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-hydroxy-2-methyl-2-propenyl)furan

: 244058-02-4
2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan

Guidance literature:: With dmap; In pyridine; for 1h; Ambient temperature;
DOI:10.1021/jo990376z

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 244058-02-4
2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / LiN(TMS)2 / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature

2: 2.) PPTS / 1.) room temperature, 96 h, 2.) EtOH, 80 deg C, 35 min

3: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 96 percent / tetrahydrofuran

5: 94 percent / DMAP / pyridine / 1 h / Ambient temperature

With dmap; pyridinium p-toluenesulfonate; Dess-Martin periodane; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo990376z

Reference yield:

: 213328-01-9
8-(tert-butyl-diphenyl-silanyloxy)-2-methyl-oct-2-en-6-yn-1-ol

: 244058-02-4
2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / propionic acid / 16 h / Heating

2: 88 percent / LiN(TMS)2 / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature

3: 2.) PPTS / 1.) room temperature, 96 h, 2.) EtOH, 80 deg C, 35 min

4: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 96 percent / tetrahydrofuran

6: 94 percent / DMAP / pyridine / 1 h / Ambient temperature

With dmap; pyridinium p-toluenesulfonate; Dess-Martin periodane; propionic acid; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo990376z