(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde

Base Information

• Chemical Name: (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde
• CAS No.: 105426-71-9
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355
• Mol file: 105426-71-9.mol

Synonyms:(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde

Chemical Property of (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde

There total 1 articles about (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde 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: 30.0%

(-)-drimenol (468-68-8) → (-)-(4aS,8aS)-4,4a,5,6,7,8-hexahydro-2,5,5,8a-tetramethylnaphthalen-1(8aH)-one (25487-94-9,823785-67-7) + (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde (105426-71-9)

Guidance literature:

With Jones reagent; In acetone; at 0 - 20 ℃; for 1h;

DOI:10.3390/molecules18022029

Reference yield: 87.0%

4,5-di-O-benzyl-2-bromo-1O-diethylcarbamoylbenzenetriol (851279-14-6) + (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde (105426-71-9) → 3,4-di-benzyloxy-6-(7'-drimen-11'-ylidene)-2,4-cyclohexadienone (851279-15-7)

Guidance literature:

4,5-di-O-benzyl-2-bromo-1O-diethylcarbamoylbenzenetriol; With tert.-butyl lithium; In diethyl ether; pentane; at -80 ℃; for 0.5h;

(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde; In diethyl ether; pentane; at -80 ℃; for 0.583333h;

DOI:10.1021/ol047332j

Reference yield: 77.0%

4-bromo-3-chloro-1,2-dibenzyloxy-5-(tert-butyldimethylsilyloxy)benzene (682744-25-8) + (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde (105426-71-9) → (1S,4aS,8aS)-1-[(3,4-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-chlorophenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene (765950-79-6)

Guidance literature:

4-bromo-3-chloro-1,2-dibenzyloxy-5-(tert-butyldimethylsilyloxy)benzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1h;

(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,58a-tetramethylnaphtahelene-1-carboxaldehyde; In diethyl ether; pentane; at -78 - 0 ℃; for 2.5h;

DOI:10.1021/jo0491399

upstream raw materials:

(-)-drimenol

Downstream raw materials:

(11S,13S)-15-(4-methoxyphenoxy)labd-7-ene-11,13-diol

3,4-di-benzyloxy-6-(7'-drimen-11'-ylidene)-2,4-cyclohexadienone

(1S,4aS,8aS)-1-[(3,4-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-chlorophenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene

(4aS,6aR,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a,12b-tetramethyl-benzo[a]xanthene