6(R)-[2-[8(S)-(2(S)-methylbutyryloxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6 tetrahydro-2H-pyran-2-one

Base Information

• Chemical Name: 6(R)-[2-[8(S)-(2(S)-methylbutyryloxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6 tetrahydro-2H-pyran-2-one
• CAS No.: 123049-73-0
• Molecular Formula: C₂₄H₃₆O₅
• Molecular Weight: 404.547
• Mol file: 123049-73-0.mol

Synonyms:

Chemical Property of 6(R)-[2-[8(S)-(2(S)-methylbutyryloxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6 tetrahydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6(R)-[2-[8(S)-(2(S)-methylbutyryloxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6 tetrahydro-2H-pyran-2-one

There total 13 articles about 6(R)-[2-[8(S)-(2(S)-methylbutyryloxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6 tetrahydro-2H-pyran-2-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: 48.0%

(3R,5R)-7-[(1S,2S,6S,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3,5-dihydroxy-heptanoic acid methyl ester (158111-08-1) → 6(R)-[2-[8(S)-(2(S)-methylbutyryloxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6 tetrahydro-2H-pyran-2-one (123049-73-0,79952-44-6)

Guidance literature:

With pyridine; hydrogen fluoride; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1021/jo970444m

Reference yield:

(1S,3R,4aS,7R,8R,8aR)-5,6-Dibromo-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-decahydro-naphthalen-1-ol → 6(R)-[2-[8(S)-(2(S)-methylbutyryloxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6 tetrahydro-2H-pyran-2-one (123049-73-0,79952-44-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 44 percent / DBU / benzene / 5 h / Heating

2: 82 percent / DMAP / pyridine / 6 h / 50 °C

3: 98 percent / TBAF, AcOH / tetrahydrofuran / 1.5 h / Heating

4: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, -78 deg C, 30 min

5: 59 percent / Cs₂CO₃ / propan-2-ol / 7.5 h / Ambient temperature

6: (Ph₃P)3RhCl / benzene / 2 h / 65 °C

7: aq. HF / acetonitrile / 1.5 h / Ambient temperature

8: 1) Et₂BOMe, 2) NaBH₄ / 1) THF, MeOH, -78 deg C, 50 min, 2) THF, MeOH, -78 deg C, 2 h

9: 48 percent / HF/pyridine / acetonitrile / 1 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; Wilkinson's catalyst; oxalyl dichloride; diethyl methoxy borane; hydrogen fluoride; tetrabutyl ammonium fluoride; caesium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; pyridine; isopropyl alcohol; acetonitrile; benzene;

DOI:10.1021/jo970444m

Reference yield:

(1S,3R,4aR,7S,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol (158041-70-4) → 6(R)-[2-[8(S)-(2(S)-methylbutyryloxy)-2(S),6(S)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6 tetrahydro-2H-pyran-2-one (123049-73-0,79952-44-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / Br₂, NEt₃ / CHCl₃ / 1 h / 0 °C

2: 44 percent / DBU / benzene / 5 h / Heating

3: 82 percent / DMAP / pyridine / 6 h / 50 °C

4: 98 percent / TBAF, AcOH / tetrahydrofuran / 1.5 h / Heating

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, -78 deg C, 30 min

6: 59 percent / Cs₂CO₃ / propan-2-ol / 7.5 h / Ambient temperature

7: (Ph₃P)3RhCl / benzene / 2 h / 65 °C

8: aq. HF / acetonitrile / 1.5 h / Ambient temperature

9: 1) Et₂BOMe, 2) NaBH₄ / 1) THF, MeOH, -78 deg C, 50 min, 2) THF, MeOH, -78 deg C, 2 h

10: 48 percent / HF/pyridine / acetonitrile / 1 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; Wilkinson's catalyst; oxalyl dichloride; diethyl methoxy borane; hydrogen fluoride; tetrabutyl ammonium fluoride; bromine; caesium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; pyridine; chloroform; isopropyl alcohol; acetonitrile; benzene;

DOI:10.1021/jo970444m

upstream raw materials:

(3R,5R)-7-[(1S,2S,6S,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3,5-dihydroxy-heptanoic acid methyl ester

(1S,3R,4aR,7S,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

(1S,3S,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol

(S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-8-hydroxymethyl-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester