N⁵-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N²-carboxy-N²-(2,4-dimethoxybenzyl)-L-ornithine, N²-allyl methyl ester

Base Information

• Chemical Name: N⁵-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N²-carboxy-N²-(2,4-dimethoxybenzyl)-L-ornithine, N²-allyl methyl ester
• CAS No.: 131216-24-5
• Molecular Formula: C₄₅H₆₈N₂O₉Si
• Molecular Weight: 809.128

Synonyms:N⁵-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N²-carboxy-N²-(2,4-dimethoxybenzyl)-L-ornithine, N²-allyl methyl ester

Chemical Property of N⁵-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N²-carboxy-N²-(2,4-dimethoxybenzyl)-L-ornithine, N²-allyl methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁵-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N²-carboxy-N²-(2,4-dimethoxybenzyl)-L-ornithine, N²-allyl methyl ester

There total 8 articles about N⁵-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N²-carboxy-N²-(2,4-dimethoxybenzyl)-L-ornithine, N²-allyl methyl 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: 92.0%

N5-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N2-carboxy-N2-(2,4-dimethoxybenzyl)-L-ornithine, N2-allyl methyl ester, 2-(dimethyl acetal) (123148-47-0) → N5-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N2-carboxy-N2-(2,4-dimethoxybenzyl)-L-ornithine, N2-allyl methyl ester (131216-24-5)

Guidance literature:

With toluene-4-sulfonic acid; acetone; at 25 ℃; for 3h;

DOI:10.1021/ja00181a035

Reference yield:

[(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-dimethoxymethyl-6-ethyl-7-methyl-dodecahydro-as-indacen-3-yl]-acetaldehyde (131196-56-0) → N5-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N2-carboxy-N2-(2,4-dimethoxybenzyl)-L-ornithine, N2-allyl methyl ester (131216-24-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) triphenylphosphine / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) 15 min

2: 1.) n-butyllithium / 1.) THF, hexane, from -78 deg C to 25 deg C, 55 min, 2.) from -78 deg C to to 10 deg C, 100 min

3: K₂CO₃ / H₂O; methanol / 4 h / 43 °C

4: tetrahydrofuran / 0.83 h / 25 °C

5: 86 mg / 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 16 h

6: 92 percent / acetone, p-toluenesulfonic acid / 3 h / 25 °C

With dmap; n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; triphenylphosphine; acetone; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00181a035

Reference yield:

tert-Butyl-[(2R,3R,3aS,4R,5aS,6R,7R,8aS,8bR)-6-(3,3-dibromo-allyl)-7-dimethoxymethyl-3-ethyl-2-methyl-dodecahydro-as-indacen-4-yloxy]-dimethyl-silane (131196-57-1) → N5-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N2-carboxy-N2-(2,4-dimethoxybenzyl)-L-ornithine, N2-allyl methyl ester (131216-24-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-butyllithium / 1.) THF, hexane, from -78 deg C to 25 deg C, 55 min, 2.) from -78 deg C to to 10 deg C, 100 min

2: K₂CO₃ / H₂O; methanol / 4 h / 43 °C

3: tetrahydrofuran / 0.83 h / 25 °C

4: 86 mg / 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 16 h

5: 92 percent / acetone, p-toluenesulfonic acid / 3 h / 25 °C

With dmap; n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; acetone; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00181a035

upstream raw materials:

N⁵-<4-<(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N²-carboxy-N²-(2,4-dimethoxybenzyl)-L-ornithine, N²-allyl methyl ester, 2-(dimethyl acetal)

[(2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-dimethoxymethyl-6-ethyl-7-methyl-dodecahydro-as-indacen-3-yl]-acetaldehyde

tert-Butyl-[(2R,3R,3aS,4R,5aS,6R,7R,8aS,8bR)-6-(3,3-dibromo-allyl)-7-dimethoxymethyl-3-ethyl-2-methyl-dodecahydro-as-indacen-4-yloxy]-dimethyl-silane

methyl (2R,3R,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-6-ethyl-2-formyldodecahydro-7-methyl-as-indacene-3-tetrolate 2-(dimethyl acetal)

Downstream raw materials:

N⁵-<4-<(2S,3S,3aS,5R,5aS,6R,7R,8aR,8bS)-5-(tert-butyldimethylsiloxy)-2-<(E)-2-(2,2-dimethyl-4-oxo-m-dioxin-6-yl)vinyl>-6-ethyldodecahydro-7-methyl-as-indacen-3-yl>tetroloyl>-N²-(2,4-dimethoxybenzyl)-L-ornithine N²-allyl methyl ester

(+)-ikarugamycin

C₃₈H₄₈N₂O₆

methyl (2R,3R,3aS,4R,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)-15-(2,4-dimethoxybenzyl)-3-ethyl-2,3,3a,4,5,5a,5b,6,9,10,11,12,13,14,15,16,17,18,20a,21,21a,21b-docosahydro-4-hydroxy-2-methyl-9,16,18-trioxo-1H-as-indacene<3,2-k><1,6>-diazacycloheptadecine-14-ca.

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