5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

Base Information

• Chemical Name: 5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
• CAS No.: 142628-53-3
• Molecular Formula: C28H38 O5
• Molecular Weight: 454.607
• Nikkaji Number: J511.512D
• Mol file: 142628-53-3.mol

Synonyms:5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde;2,4,6-Trihydroxy-5-[3-methyl-1-(1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl)butyl]benzene-1,3-dicarbaldehyde;Macrocarpal G;SCHEMBL4411392

Chemical Property of 5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

Chemical Property:

• Vapor Pressure: 5.25E-11mmHg at 25°C
• Boiling Point: 509.6°Cat760mmHg
• Flash Point: 276.1°C
• PSA: 94.83000
• Density: 1.2g/cm³
• LogP: 6.21280
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 454.27192431
• Heavy Atom Count: 33
• Complexity: 767

Purity/Quality:

98%min ^*data from raw suppliers

MacrocarpalC 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C1=C(C(=C(C(=C1O)C=O)O)C=O)O)C2(CCC3C2C4C(C4(C)C)CCC3=C)C

Technology Process of 5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

There total 13 articles about 5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde 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: 87.0%

2,4,6-trihydroxy-5-((R)-1-((1aR,4R,4aR,7S,7aS,7bR)-4-hydroxy-1,1,4,7-tetramethyldecahydro-1H-cyclopropa[e]azulen-7-yl)-3-methylbutyl)isophthalaldehyde (142698-60-0,144372-45-2,132951-90-7) → 2,4,6-trihydroxy-5-((R)-3-methyl-1-((1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylenedecahydro-1Hcyclopropa[e]azulen-7-yl)butyl)isophthalaldehyde (142628-53-3)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 2,5-di-tert-butylpyridine; In tetrahydrofuran; ethyl acetate; for 6h; Reagent/catalyst; Temperature; Solvent; regioselective reaction; Inert atmosphere; Reflux;

DOI:10.1021/np400869z

Reference yield: 58.0%

(+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.02,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalaldehyde (201207-55-8) → 2,4,6-trihydroxy-5-((R)-3-methyl-1-((1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylenedecahydro-1Hcyclopropa[e]azulen-7-yl)butyl)isophthalaldehyde (142628-53-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium p-toluenethiolate; In toluene; Heating;

DOI:10.1039/a705231f

Reference yield:

(-)-(1S,2R,4R,7S)-10-(tert-butyldimethylsiloxy)-7-<(tert-butyldimethylsiloxy)methyl>-3,3,11-trimethyltricyclo<6.3.0.02,4>undeca-8,10-diene (201207-43-4) → 2,4,6-trihydroxy-5-((R)-3-methyl-1-((1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylenedecahydro-1Hcyclopropa[e]azulen-7-yl)butyl)isophthalaldehyde (142628-53-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 33 percent / ZnCl₂ / CH₂Cl₂ / 1 h / Ambient temperature; further reagent and conditions

2: 88 percent / H₂ / Pd/C / methanol / 27 h / 3800 Torr / Ambient temperature

3: 96 percent / NaBH₄ / methanol / 1 h / Ambient temperature

4: 100 percent / DMAP / CH₂Cl₂ / 1 h / Ambient temperature

5: 1.) 2-nitrophenyl selenocyanate, n-Bu₃P, 2.) aq. H₂O₂ / 1) THF, 75 deg C, 20 h; 2) THF, rt, 3 h

6: NaOMe / methanol / 6.5 h / Ambient temperature

7: 100 percent / H₂ / Pd/C / methanol / 15 h / 3800 Torr / Ambient temperature

8: 1.) 2-nitrophenyl selenocyanate, n-Bu₃P, 2.) aq. H₂O₂ / 1) THF, 50 deg C, 12 h; 2) THF, rt, 30 min

9: 100 percent / DIBALH / toluene / 1 h / -78 °C

10: 87 percent / N-methylmorpholine N-oxide, 4 Angstroem molecular sieves, tetra-n-propylammonium perruthenate / acetonitrile / 1 h / Ambient temperature

11: 58 percent / lithium p-thiocresolate / hexamethylphosphoric acid triamide; toluene / 5 h / Heating

With dmap; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; tetrapropylammonium perruthennate; tributylphosphine; lithium p-thiocresolate; 4 A molecular sieve; hydrogen; dihydrogen peroxide; sodium methylate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; zinc(II) chloride; palladium on activated charcoal; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo981413+

upstream raw materials:

(+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalaldehyde

(+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxybenzene-1,3-dimethanol

(1aR,4S,7R,7aR,7bR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-1,1,7-trimethyl-1a,3,4,7,7a,7b-hexahydro-1H,2H-cyclopropa[e]azulen-6-one

(-)-(1S,2R,4R,7S)-10-(tert-butyldimethylsiloxy)-7-<(tert-butyldimethylsiloxy)methyl>-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undeca-8,10-diene

Downstream raw materials:

C₃₅H₅₂O₈

C₃₅H₅₂O₈

(1aR,4R,4aR,7S,7aS,7bR)-7-[(R)-1-(3,5-Bis-hydroxymethyl-2,4,6-trimethoxy-phenyl)-3-methyl-butyl]-1,1,4,7-tetramethyl-decahydro-cyclopropa[e]azulen-4-ol

(+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxybenzene-1,3-dimethanol

Refernces

• 1、 Tanaka, Tetsuaki,Mikamiyama, Hidenori,Maeda, Kimiya,Iwata, Chuzo,In, Yasuko,Ishida, Toshimasa. "Total synthesis of (-)-macrocarpal C. Stereoselective coupling reaction with a novel hexasubstituted benzene Cr(CO)3 complex as a biomimetic chiral benzyl cation equivalent". . p. 9782 - 9793. Retrieved 2007/10/03.