(+)-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

Base Information

• Chemical Name: (+)-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
• CAS No.: 201207-45-6
• Molecular Formula: C₃₉H₆₀O₉Si
• Molecular Weight: 700.986

Synonyms:(+)-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

Chemical Property of (+)-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

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Technology Process of (+)-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

There total 4 articles about (+)-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 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:

(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'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:

Multi-step reaction with 2 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

With triethylamine; zinc(II) chloride; In 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'-((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.) CH₂Cl₂, 2.) MeOH, 0 deg C;

DOI:10.1039/a705231f

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

(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:

(-)-dimethyl 5-<(1'S)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyl-10-oxotricyclo<6.3.0.0^2,4>undec-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

(-)-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

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