2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propyl}-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propyl}-malonic acid dimethyl ester
• CAS No.: 172147-72-7
• Molecular Formula: C₄₁H₅₂O₁₀
• Molecular Weight: 704.858
• Mol file: 172147-72-7.mol

Synonyms:

Chemical Property of 2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propyl}-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propyl}-malonic acid dimethyl ester

There total 4 articles about 2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propyl}-malonic acid dimethyl 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:

(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol (162222-93-7) → 2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propyl}-malonic acid dimethyl ester (172147-72-7)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 20 h

2: <(C₆H₅)3P>RhCl / ethanol; H₂O / 1 h / Heating

3: BrCCl₂CCl₂Br, PPh₃, Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

4: K₂CO₃, dibenzo-18-crown-6 / 5 h / 80 °C

With Wilkinson's catalyst; dibenzo-18-crown-6; 1,2-dibromo-1,1,2,2-tetrachloroethane; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00214-X

Reference yield:

3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propan-1-ol (172147-70-5) → 2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propyl}-malonic acid dimethyl ester (172147-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1: BrCCl₂CCl₂Br, PPh₃, Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

2: K₂CO₃, dibenzo-18-crown-6 / 5 h / 80 °C

With dibenzo-18-crown-6; 1,2-dibromo-1,1,2,2-tetrachloroethane; potassium carbonate; triethylamine; triphenylphosphine; In dichloromethane;

DOI:10.1016/S0960-894X(97)00214-X

Reference yield:

(2S,3S,4R,5R,6S)-2-[(1R,2R)-2-(3-Allyloxy-propoxy)-cyclohexyloxy]-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran (172147-69-2) → 2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propyl}-malonic acid dimethyl ester (172147-72-7)

Guidance literature:

Multi-step reaction with 3 steps

1: <(C₆H₅)3P>RhCl / ethanol; H₂O / 1 h / Heating

2: BrCCl₂CCl₂Br, PPh₃, Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

3: K₂CO₃, dibenzo-18-crown-6 / 5 h / 80 °C

With Wilkinson's catalyst; dibenzo-18-crown-6; 1,2-dibromo-1,1,2,2-tetrachloroethane; potassium carbonate; triethylamine; triphenylphosphine; In ethanol; dichloromethane; water;

DOI:10.1016/S0960-894X(97)00214-X

upstream raw materials:

malonic acid dimethyl ester

(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol

3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-propan-1-ol

(2S,3S,4R,5R,6S)-2-[(1R,2R)-2-(3-Allyloxy-propoxy)-cyclohexyloxy]-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran