(1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate

Base Information

• Chemical Name: (1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate
• CAS No.: 128684-89-9
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.224
• Mol file: 128684-89-9.mol

Synonyms:(1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate

Chemical Property of (1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate

There total 24 articles about (1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate 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: 91.0%

methyl (1R,3R,4R)-4-benzoyloxy-3-methoxycyclohexane-1-carboxylate (133429-54-6) → (1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate (128684-89-9)

Guidance literature:

methyl (1R,3R,4R)-4-benzoyloxy-3-methoxycyclohexane-1-carboxylate; With methanol; sodium methylate; at 20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In methanol; water; Inert atmosphere;

DOI:10.1016/j.tet.2009.06.030

Reference yield: 50.0%

4-Acetoxy-3-methoxy-cyclohexanecarboxylic acid methyl ester (130677-94-0,130793-41-8) → (1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate (128684-89-9) + (1S,3S,4S)-4-Acetoxy-3-methoxy-cyclohexanecarboxylic acid methyl ester (130793-41-8)

Guidance literature:

With Pseudomonas sp. (AK) lipase; at 25 ℃; for 72h; pH 7.6;

DOI:10.1016/S0040-4039(00)89045-0

Reference yield:

(4R,5S)-5-ethenyl-4-methoxytetrahydro-2H-pyran-2-one (118207-39-9) → (1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate (128684-89-9)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 1.) -78 deg C, 90 min, 2.) 0 deg C, 60 min

2: toluene / 76 h / Heating

3: 1 N HCl / toluene; tetrahydrofuran / 3 h / Ambient temperature

4: diethyl ether; ethyl acetate

5: 1.) a) BH₃, 2.) 30percent H₂O₂, 3 N NaOH / 1.) a) THF, -78 deg C, 30 min, b) 0 deg C, 90 min, 2.) THF, RT, 3 h

With hydrogenchloride; sodium hydroxide; borane; dihydrogen peroxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ja00170a024

upstream raw materials:

methanol

(1S,3S,4R) methyl 3,4-epoxy-1-cyclohexanecarboxylate

methyl (1R,3R)-3-methoxycyclohex-4-enecarboxylate

4-Acetoxy-3-methoxy-cyclohexanecarboxylic acid methyl ester

Downstream raw materials:

(-)-(1R,2R,4R)-4-hydroxymethyl-2-methoxycyclohexan-1-ol

(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexanecarboxaldehyde

(E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal

(1R,3R,4R)-3-methoxy-1-methoxycarbonyl-4-((trimethylsilylethoxy)methoxy)cyclohexane