(4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one

Base Information

• Chemical Name: (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one
• CAS No.: 257941-62-1
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.247
• Mol file: 257941-62-1.mol

Synonyms:(4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one

Chemical Property of (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one

There total 3 articles about (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-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: 50.0%

Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1) → (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one (878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9) + (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one (257941-62-1)

Guidance literature:

With glucose dehydrogenase; 7α-hydroxysteroid dehydrogenase from extremophilic bacterium Deinococcus marmoris strain; NADPH; In aq. phosphate buffer; dimethyl sulfoxide; at 25 ℃; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/ejoc.202100174

Reference yield: 35.0%

Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1) → 9a-methyl-4,5,9,9a-tetrahydro-3H,8H-benzo[b]oxepine-2,7-dione + (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione (33878-99-8) + (R)-Wieland-Miescher ketone (100348-93-4) + (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one (257941-62-1)

Guidance literature:

With α-D-glucose 6-phosphate; oxygen; NADP; glucose-6-phosphate dehydrogenase; recombinant c-hexanone monooxygenase (E_. coli TOP₁₀ pQR₂₃₉); In phosphate buffer; at 20 ℃; for 26h; pH=8.7; Further byproducts given;

DOI:10.1002/adsc.200505027

Reference yield:

Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1) → (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione (33878-99-8) + (4αR,5S)-5-hydroxy-4α-methyl-4,4α,5,6,7,8-hexahydronaphthalen-2(3H)-one (257941-62-1)

Guidance literature:

With D-glucose; yeast cells of Candida melibiosica IAM₄₄₈₈; In phosphate buffer; at 30 ℃; for 68h; pH=6.5; Enzymatic reaction;

DOI:10.1021/jo991192n

upstream raw materials:

Wieland-Miescher ketone

Downstream raw materials:

(R)-Wieland-Miescher ketone