7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

Base Information

Chemical Name:7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester
CAS No.:440677-21-4
Molecular Formula:C₄₇H₇₁NO₈Si
Molecular Weight:806.168
Hs Code.:

7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

Synonyms:7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

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Chemical Property of 7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

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Technology Process of 7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

There total 18 articles about 7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl 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: 85.0%

: 440677-20-3
(6R,7S)-8-Methyl-7-{(E)-2-methyl-5-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-3-oxo-pent-1-enyl}-1-oxo-9-((S)-5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

: 440677-21-4
7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

Guidance literature:: With dimethylsulfide borane complex; (R)-(+)-tetrahydro-1-methyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; In toluene; at -10 ℃; for 0.166667h;
DOI:10.1055/s-2002-20450

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 440677-21-4
7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 89 percent / NaH / tetrahydrofuran / 5 h / 25 °C

2.1: i-Pr₂NEt / CH₂Cl₂ / 2 h / 25 °C

3.1: CH₂Cl₂ / 12 h / 25 °C

3.2: MeI / tetrahydrofuran / 2 h / 25 °C

4.1: 89 percent / 3 Angstroem molecular sieves / (-)-siam*Cu(SbF₆)2 / CH₂Cl₂ / 36 h / 25 °C

5.1: 50 percent / PTS*H₂O / tetrahydrofuran; H₂O / 0.5 h / 25 °C

6.1: 90 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 25 °C

7.1: 55 percent / LiCl; i-Pr₂NEt / acetonitrile / 2 h / 0 °C

8.1: 85 percent / (R)-B-Me-CBS; BMS / toluene / 0.17 h / -10 °C

With dimethylsulfide borane complex; 3 A molecular sieve; PTS*H₂O; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; (R)-(+)-tetrahydro-1-methyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (-)-siam*Cu(SbF₆)2; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; 4.1: asymmetric Diels-Alder reaction / 7.1: Horner-Wadsworth-Emmons reaction / 8.1: Corey-Bakshi-Shibata asymmetric reduction;
DOI:10.1055/s-2002-20450

Reference yield:

: 440677-05-4
(S)-5-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-1-methylene-but-2-enyl]-dihydro-furan-2-one

: 440677-21-4
7-{3-hydroxy-2-methyl-5-[4-methyl-5-(1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-pent-1-enyl}-8-methyl-1-oxo-9-(5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / 3 Angstroem molecular sieves / (-)-siam*Cu(SbF₆)2 / CH₂Cl₂ / 36 h / 25 °C

2: 50 percent / PTS*H₂O / tetrahydrofuran; H₂O / 0.5 h / 25 °C

3: 90 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 25 °C

4: 55 percent / LiCl; i-Pr₂NEt / acetonitrile / 2 h / 0 °C

5: 85 percent / (R)-B-Me-CBS; BMS / toluene / 0.17 h / -10 °C

With dimethylsulfide borane complex; 3 A molecular sieve; PTS*H₂O; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; (R)-(+)-tetrahydro-1-methyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (-)-siam*Cu(SbF₆)2; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; 1: asymmetric Diels-Alder reaction / 4: Horner-Wadsworth-Emmons reaction / 5: Corey-Bakshi-Shibata asymmetric reduction;
DOI:10.1055/s-2002-20450