2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester
• CAS No.: 182625-00-9
• Molecular Formula: C₂₂H₄₀O₇
• Molecular Weight: 416.555

Synonyms:2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester

There total 8 articles about 2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-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: 75.0%

pivaloyl chloride (3282-30-2) + [(1S,2S,3R,6S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxymethyl-3-methoxymethoxymethyl-1-methyl-cyclohexyl]-methanol (182624-80-2) → 2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester (182625-00-9)

Guidance literature:

In pyridine; at 0 ℃;

DOI:10.1016/0040-4039(96)01585-7

Reference yield:

ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methyl-2-propenoate (127642-52-8) → 2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester (182625-00-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 74 percent / LDA / tetrahydrofuran / -78 °C

2: NaBH₄ / methanol / 0 °C

3: pyridine / 0 °C

4: DBU / toluene / 100 °C

5: 1.) O₃, pyridine, Me₂S; 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C; 2.) 0 deg C

6: 99 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 50 °C

7: 88 percent / LiAlH₄ / tetrahydrofuran / 0 °C

8: 75 percent / pyridine / 0 °C

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; dimethylsulfide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; 1,2-dichloro-ethane; toluene;

DOI:10.1016/0040-4039(96)01585-7

Reference yield:

(3aS,6R,7S,7aS)-7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxymethyl-7a-methyl-hexahydro-isobenzofuran-1-one (182624-78-8) → 2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester (182625-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 50 °C

2: 88 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3: 75 percent / pyridine / 0 °C

With lithium aluminium tetrahydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane;

DOI:10.1016/0040-4039(96)01585-7

upstream raw materials:

pivaloyl chloride

[(1S,2S,3R,6S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxymethyl-3-methoxymethoxymethyl-1-methyl-cyclohexyl]-methanol

ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methyl-2-propenoate

(3aS,6R,7S,7aS)-7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxymethyl-7a-methyl-hexahydro-isobenzofuran-1-one

Downstream raw materials:

2,2-Dimethyl-propionic acid (1S,2S,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxymethyl-2-methyl-cyclohexylmethyl ester

(1S,2R,3S,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxymethyl-2-methyl-cyclohexanecarbaldehyde

[(1S,2S,3S,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxymethyl-2-methyl-cyclohexyl]-methanol

[(1R,2S,3S,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxymethyl-2-methyl-cyclohexyl]-methanol

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