6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane

Base Information

• Chemical Name: 6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane
• CAS No.: 126615-48-3
• Molecular Formula: C₃₂H₄₈O₆
• Molecular Weight: 528.73
• Mol file: 126615-48-3.mol

Synonyms:

Chemical Property of 6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane

There total 19 articles about 6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane 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:

1-Methoxy-4-(1-methoxy-vinyl)-benzene (51440-56-3) → 6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane (126615-48-3,126721-02-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / pyridinium tosylate / molecular sieve / CH₂Cl₂ / 1 h

2: 1) O₃ 2) LiAlH₄ / 1) MeOH, AcOEt, -78 deg C 2) Et₂O, r.t.

3: 1) DMSO, oxalyl chloride 2) Et₃N / 1) CH₂Cl₂, 20 min, -78 deg C 2) a) 20 min, -78 deg C b) 10 min, 0 deg C

4: 50 mg / diethyl ether / 1) 45 min, 0 deg C 2) 30 min, r.t.

5: n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

6: 1) oxalyl chloride, DMSO 2) Et₃N / 1) CH₂Cl₂, 30 min, -78 deg C 2) a) 15 min, -78 deg C b) 10 min, 0 deg C

7: 1) LDA / 1) THF, -78 deg C, 1h 2) -78 deg C, 20 min

8: 1) oxalyl chloride, DMSO 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 45 min 2) 20 min, -78 deg C

With lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00296a044

Reference yield:

4(S)-<1(S)-Methyl-2-cyanoethyl>-2,2,5(R)-trimethyl-1,3-dioxane (126720-95-4) → 6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane (126615-48-3,126721-02-6)

Guidance literature:

Multi-step reaction with 14 steps

1: HCl / methanol / Heating

3: LDA

4: 2) (Ph₃P)4Pd / 1) appropriate sodium salt

5: decarbomethoxylation

6: Lit_.: Ziegler, F_. E_.; Cain, W_. T_. J_. Org_. Chem_. 1989, 54, 3347

7: 94 percent / pyridinium tosylate / molecular sieve / CH₂Cl₂ / 1 h

8: 1) O₃ 2) LiAlH₄ / 1) MeOH, AcOEt, -78 deg C 2) Et₂O, r.t.

9: 1) DMSO, oxalyl chloride 2) Et₃N / 1) CH₂Cl₂, 20 min, -78 deg C 2) a) 20 min, -78 deg C b) 10 min, 0 deg C

10: 50 mg / diethyl ether / 1) 45 min, 0 deg C 2) 30 min, r.t.

11: n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

12: 1) oxalyl chloride, DMSO 2) Et₃N / 1) CH₂Cl₂, 30 min, -78 deg C 2) a) 15 min, -78 deg C b) 10 min, 0 deg C

13: 1) LDA / 1) THF, -78 deg C, 1h 2) -78 deg C, 20 min

14: 1) oxalyl chloride, DMSO 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 45 min 2) 20 min, -78 deg C

With hydrogenchloride; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00296a044

Reference yield:

3(S)-<1(R),4-Dimethyl-2(E)-pentenyl>-4(S)-methyl-5(S)-<1(R)-methyl-2-hydroxyethyl>dihydro-2(3H)-furanone (126615-39-2) → 6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane (126615-48-3,126721-02-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 0.83 g / DMAP, Et₃N / CH₂Cl₂ / 13 h / Ambient temperature

2: Lit_.: Ziegler, F_. E_.; Cain, W_. T_. J_. Org_. Chem_. 1989, 54, 3347

3: 94 percent / pyridinium tosylate / molecular sieve / CH₂Cl₂ / 1 h

4: 1) O₃ 2) LiAlH₄ / 1) MeOH, AcOEt, -78 deg C 2) Et₂O, r.t.

5: 1) DMSO, oxalyl chloride 2) Et₃N / 1) CH₂Cl₂, 20 min, -78 deg C 2) a) 20 min, -78 deg C b) 10 min, 0 deg C

6: 50 mg / diethyl ether / 1) 45 min, 0 deg C 2) 30 min, r.t.

7: n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

8: 1) oxalyl chloride, DMSO 2) Et₃N / 1) CH₂Cl₂, 30 min, -78 deg C 2) a) 15 min, -78 deg C b) 10 min, 0 deg C

9: 1) LDA / 1) THF, -78 deg C, 1h 2) -78 deg C, 20 min

10: 1) oxalyl chloride, DMSO 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 45 min 2) 20 min, -78 deg C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00296a044

upstream raw materials:

1-Methoxy-4-(1-methoxy-vinyl)-benzene

(E)-1-bromo-2-methylpent-2-ene

(E)-(4R)-4,6-dimethyl-non-6-en-3-one

(4α,5β)-4,5-dihydro-5-(2-hydroxy-1-methylethyl)-4-methyl-2(3H)-furanone

Downstream raw materials:

Denticulatin B

Denticulatin A