(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

Base Information

• Chemical Name: (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
• CAS No.: 175985-37-2
• Molecular Formula: C₂₁H₃₆O₂Si
• Molecular Weight: 348.601

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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: 32.0%

(-)-(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-chloro-3-methyl-butyl)-2,4,6-trimethoxy-isophthalic acid dimethyl ester → (1aR,4S,7S,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 (176199-13-6) + (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'-((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 + (+)-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)

Guidance literature:

With zinc(II) chloride; In dichloromethane; for 1h; Ambient temperature; further reagent and conditions;

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) → (1aR,4S,7S,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 (176199-13-6) + (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'-((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

Guidance literature:

With ammonium cerium(IV) nitrate; zinc(II) chloride; Yield given; Multistep reaction. Yields of byproduct given; 1) Et₂O, CH₂Cl₂, rt; 2) MeOH;

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) → (1aR,4S,7S,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 (176199-13-6) + (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'-((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 + (+)-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)

Guidance literature:

With ammonium cerium(IV) nitrate; zinc(II) chloride; Yield given; Multistep reaction. Yields of byproduct given; 1) Et₂O, CH₂Cl₂, rt, 1.5 h; 2) MeOH, 0 deg C, 30 min;

DOI:10.1021/jo981413+

upstream raw materials:

(-)-(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:

(+)-aromadendrene

(+)-dimethyl 5-<(1'S)-1'-((1S,2R,4R,7S,11R)-7-<(tert-butyldimethylsiloxy)methyl>-3,3,11-trimethyl-10-oxotricyclo<6.3.0.0^2,4>undec-8-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate

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

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

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