(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

Base Information

Chemical Name:(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
CAS No.:440677-20-3
Molecular Formula:C₄₇H₆₉NO₈Si
Molecular Weight:804.152
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 16 articles about (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 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: 55.0%

: 7-Formyl-8-methyl-1-oxo-9-((S)-5-oxo-tetrahydro-furan-2-yl)-2-aza-spiro[5.5]undec-8-ene-2-carboxylic acid benzyl ester

: 440677-12-3
{1-Methyl-4-[(2R,4R,5R)-4-methyl-5-((E)-1-methyl-3-triisopropylsilanyloxy-propenyl)-tetrahydro-furan-2-yl]-2-oxo-butyl}-phosphonic acid diethyl ester

: 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

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 0 ℃; for 2h;
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

: 440677-20-3
(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

Guidance literature:: Multi-step reaction with 4 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

With 3 A molecular sieve; PTS*H₂O; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; (-)-siam*Cu(SbF₆)2; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: asymmetric Diels-Alder reaction / 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2002-20450

Reference yield:

: 56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
L-glutamic acid

: 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

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaNO₂; aq. HCl / 20 h / 25 °C

1.2: SOCl₂ / 12 h / 80 °C

1.3: Pd(PPh₃)4 / 1,2-dichloro-ethane / 20 h / 65 °C

2.1: 96 percent / tetrahydrofuran / 0.03 h / -10 °C

3.1: 89 percent / 3 Angstroem molecular sieves / (-)-siam*Cu(SbF₆)2 / CH₂Cl₂ / 36 h / 25 °C

4.1: 50 percent / PTS*H₂O / tetrahydrofuran; H₂O / 0.5 h / 25 °C

5.1: 90 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 25 °C

6.1: 55 percent / LiCl; i-Pr₂NEt / acetonitrile / 2 h / 0 °C

With hydrogenchloride; 3 A molecular sieve; PTS*H₂O; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; sodium nitrite; (-)-siam*Cu(SbF₆)2; In tetrahydrofuran; dichloromethane; water; acetonitrile; 3.1: asymmetric Diels-Alder reaction / 6.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2002-20450