(-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate

Base Information

• Chemical Name: (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate
• CAS No.: 219954-67-3
• Molecular Formula: C₃₃H₄₈O₈
• Molecular Weight: 572.739

Synonyms:(-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate

Chemical Property of (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate

There total 6 articles about (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 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:

(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) → (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.02,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate (219954-67-3)

Guidance literature:

Multi-step reaction with 7 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

With dmap; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; tributylphosphine; hydrogen; dihydrogen peroxide; sodium methylate; triethylamine; zinc(II) chloride; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo981413+

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) → (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.02,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate (219954-67-3)

Guidance literature:

Multi-step reaction with 6 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

With dmap; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; tributylphosphine; hydrogen; dihydrogen peroxide; sodium methylate; zinc(II) chloride; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jo981413+

Reference yield:

(+)-dimethyl 5-<(1'S)-1'-((1S,2R,4R,7S,11R)-7-<(tert-butyldimethylsiloxy)methyl>-3,3,11-trimethyl-10-oxotricyclo<6.3.0.02,4>undec-8-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate (201207-45-6) → (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.02,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate (219954-67-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / H₂ / Pd/C / methanol / 27 h / 3800 Torr / Ambient temperature

2: 96 percent / NaBH₄ / methanol / 1 h / Ambient temperature

3: 100 percent / DMAP / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) 2-nitrophenyl selenocyanate, n-Bu₃P, 2.) aq. H₂O₂ / 1) THF, 75 deg C, 20 h; 2) THF, rt, 3 h

5: NaOMe / methanol / 6.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; tributylphosphine; hydrogen; dihydrogen peroxide; sodium methylate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jo981413+

upstream raw materials:

5-[(R)-1-((1aR,4S,4aR,7S,7aR,7bR)-4-Acetoxymethyl-1,1,7-trimethyl-1a,2,3,4,4a,7,7a,7b-octahydro-1H-cyclopropa[e]azulen-7-yl)-3-methyl-butyl]-2,4,6-trimethoxy-isophthalic acid dimethyl ester

(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

(+)-dimethyl 5-<(1'S)-1'-((1R,2R,4R,7S,8R,10S,11S)-10-hydroxy-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate

Downstream raw materials:

(-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate

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

(+)-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

(+)-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

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