2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-{2-[(2R,4R,6S)-4-acetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-{2-[(2R,4R,6S)-4-acetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester
• CAS No.: 156741-23-0
• Molecular Formula: C₃₄H₅₄O₈S
• Molecular Weight: 622.864
• Mol file: 156741-23-0.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-{2-[(2R,4R,6S)-4-acetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-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-[(2R,4R,6S)-4-acetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester

There total 9 articles about 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-{2-[(2R,4R,6S)-4-acetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-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: 15.0%

acetic anhydride (108-24-7) + 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-{2-[(2R,4R,6S)-4-hydroxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester → 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-((2R,4R,6S)-4-acetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester + 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-{2-[(2R,4R,6S)-4-acetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester (156741-23-0)

Guidance literature:

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

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-[(2R,4R,6S)-4-acetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester (156741-23-0)

Guidance literature:

Multi-step reaction with 8 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

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; methyl iodide; In tetrahydrofuran; N,N-dimethyl-formamide; 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-[(2R,4R,6S)-4-acetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-6-propyl-cyclohexylmethyl ester (156741-23-0)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; carbon disulfide; hydrogen fluoride; tri-n-butyl-tin hydride; sodium hydride; lithium 4,4′-di-tert-butylbiphenylide; methyl iodide; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

acetic anhydride

(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-((2R,4R,6S)-4-acetoxy-6-iodomethyl-tetrahydro-pyran-2-yl)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

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