2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6S)-6-allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6S)-6-allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester
• CAS No.: 156741-25-2
• Molecular Formula: C₂₈H₅₀O₄
• Molecular Weight: 450.703
• Mol file: 156741-25-2.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6S)-6-allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6S)-6-allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

There total 10 articles about 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6S)-6-allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester 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:

(1S,3S,5R)-6,8-dioxabicyclo[3.2.1]octan-3-yl acetate (53716-84-0) → 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6S)-6-allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester (156741-25-2)

Guidance literature:

Multi-step reaction with 12 steps

1: BF₃*Et₂O

2: MeONa

3: ImH / dimethylformamide

4: lithium 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

5: 1.) NaH, CS₂, 2.) MeI, 3.) Bu₃SnH / 2.) THF

6: aq. HF / acetonitrile

7: 48 h / 40 °C

9: LiI / hexamethylphosphoric acid triamide; toluene / Heating

10: Zn / methanol / Heating

11: K₂CO₃ / methanol / Ambient temperature

12: CSA / acetone

With 1H-imidazole; carbon disulfide; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; lithium 4,4′-di-tert-butylbiphenylide; potassium carbonate; lithium iodide; zinc; methyl iodide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)75798-4

Reference yield:

Acetic acid (2S,4S)-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester → 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6S)-6-allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester (156741-25-2)

Guidance literature:

Multi-step reaction with 11 steps

1: MeONa

2: ImH / dimethylformamide

3: lithium 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

4: 1.) NaH, CS₂, 2.) MeI, 3.) Bu₃SnH / 2.) THF

5: aq. HF / acetonitrile

6: 48 h / 40 °C

8: LiI / hexamethylphosphoric acid triamide; toluene / Heating

9: Zn / methanol / Heating

10: K₂CO₃ / methanol / Ambient temperature

11: CSA / acetone

With 1H-imidazole; carbon disulfide; hydrogen fluoride; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; lithium 4,4′-di-tert-butylbiphenylide; potassium carbonate; lithium iodide; zinc; methyl iodide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)75798-4

Reference yield:

(2S,4S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol → 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6S)-6-allyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester (156741-25-2)

Guidance literature:

Multi-step reaction with 10 steps

1: ImH / dimethylformamide

2: lithium 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

3: 1.) NaH, CS₂, 2.) MeI, 3.) Bu₃SnH / 2.) THF

4: aq. HF / acetonitrile

5: 48 h / 40 °C

7: LiI / hexamethylphosphoric acid triamide; toluene / Heating

8: Zn / methanol / Heating

9: K₂CO₃ / methanol / Ambient temperature

10: CSA / acetone

With 1H-imidazole; carbon disulfide; hydrogen fluoride; tri-n-butyl-tin hydride; sodium hydride; lithium 4,4′-di-tert-butylbiphenylide; potassium carbonate; lithium iodide; zinc; methyl iodide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)75798-4

upstream raw materials:

2,2-dimethoxy-propane

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-((3R,5S)-3,5-dihydroxy-oct-7-enyl)-3-methyl-6-propyl-cyclohexylmethyl ester

(1S,3S,5R)-6,8-dioxabicyclo[3.2.1]octan-3-yl acetate

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((2R,4R,6S)-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

Downstream raw materials:

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((4R,6R)-6-methoxycarbonylmethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-{2-[(4R,6R)-2,2-dimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester