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Cas Database

1000009-66-4

1000009-66-4

Identification

  • Product Name:(1S,2R,4aS,8aS)-1-[hydroxy(3-methoxy-5-methylphenyl)methyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

  • CAS Number: 1000009-66-4

  • EINECS:

  • Molecular Weight:360.537

  • Molecular Formula: C23H36O3

  • HS Code:

  • Mol File:1000009-66-4.mol

Synonyms:(1S,2R,4aS,8aS)-1-[hydroxy(3-methoxy-5-methylphenyl)methyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

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Relevant articles and documentsAll total 1 Articles be found

Synthesis of SHIP1-activating analogs of the sponge meroterpenoid pelorol

Meimetis, Labros G.,Nodwell, Matt,Yang, Lu,Wang, Xiaoxia,Patrick, Brian O.,Andersen, Raymond J.,Wu, Joyce,Harwig, Curtis,Stenton, Grant R.,MacKenzie, Lloyd F.,MacRury, Thomas,Ming-Lum, Andrew,Ong, Christopher J.,Mui, Alice L. -F.,Krystal, Gerald

, p. 5195 - 5207,13 (2012)

Two biomimetic approaches have been used to synthesize analogs of the SHIP1-activating sponge meroterpenoid pelorol (1). One approach started from the chiral pool plant natural product sclareolide, which has the same absolute configuration as pelorol. The

Process route upstream and downstream products

Process route

3-bromo-5-methoxytoluene
29578-83-4

3-bromo-5-methoxytoluene

(1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde
52618-00-5

(1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde

(1S,2R,4aS,8aS)-1-[hydroxy(3-methoxy-5-methylphenyl)methyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
1000009-66-4

(1S,2R,4aS,8aS)-1-[hydroxy(3-methoxy-5-methylphenyl)methyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

Conditions
Conditions Yield
3-bromo-5-methoxytoluene; With tert.-butyl lithium; In tetrahydrofuran; at -78 - 20 ℃; for 0.5h;
(1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde; In tetrahydrofuran; at -78 ℃; for 2h;
88%
3-bromo-5-methoxytoluene
29578-83-4

3-bromo-5-methoxytoluene

(1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde
52618-00-5

(1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde

(1S,2R,4aS,8aS)-1-[hydroxy(3-methoxy-5-methylphenyl)methyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
1000009-66-4

(1S,2R,4aS,8aS)-1-[hydroxy(3-methoxy-5-methylphenyl)methyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

Conditions
Conditions Yield
3-bromo-5-methoxytoluene; With tert.-butyl lithium; In tetrahydrofuran; at -78 - 20 ℃; for 0.5h;
(1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde; In tetrahydrofuran; at -78 ℃; for 2h;
88%

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