(+)-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

Base Information

• Chemical Name: (+)-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
• CAS No.: 201207-55-8
• Molecular Formula: C₃₁H₄₄O₅
• Molecular Weight: 496.687

Synonyms:(+)-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

Chemical Property of (+)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-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

There total 12 articles about (+)-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 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%

(+)-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-trimethoxybenzene-1,3-dimethanol (201207-54-7) → (+)-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)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In acetonitrile;

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) → (+)-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)

Guidance literature:

Multi-step reaction with 10 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

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

DOI:10.1021/jo981413+

Reference yield:

(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 (175985-37-2) → (+)-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)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / Et₃N / diethyl ether; CH₂Cl₂ / 1 h / Ambient temperature

2: 33 percent / ZnCl₂ / CH₂Cl₂ / 1 h / Ambient temperature; further reagent and conditions

3: 88 percent / H₂ / Pd/C / methanol / 27 h / 3800 Torr / Ambient temperature

4: 96 percent / NaBH₄ / methanol / 1 h / Ambient temperature

5: 100 percent / DMAP / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) 2-nitrophenyl selenocyanate, n-Bu₃P, 2.) aq. H₂O₂ / 1) THF, 75 deg C, 20 h; 2) THF, rt, 3 h

7: NaOMe / methanol / 6.5 h / Ambient temperature

8: 100 percent / H₂ / Pd/C / methanol / 15 h / 3800 Torr / Ambient temperature

9: 1.) 2-nitrophenyl selenocyanate, n-Bu₃P, 2.) aq. H₂O₂ / 1) THF, 50 deg C, 12 h; 2) THF, rt, 30 min

10: 100 percent / DIBALH / toluene / 1 h / -78 °C

11: 87 percent / N-methylmorpholine N-oxide, 4 Angstroem molecular sieves, tetra-n-propylammonium perruthenate / acetonitrile / 1 h / Ambient temperature

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

DOI:10.1021/jo981413+

upstream raw materials:

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

methyl iodide

(+)-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

Downstream 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-trimethoxybenzene-1,3-dimethanol

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

(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

C₃₅H₅₂O₈

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