(1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester
• CAS No.: 78176-53-1
• Molecular Formula: C₂₂H₂₈O₆
• Molecular Weight: 388.461
• Mol file: 78176-53-1.mol

Synonyms:(1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester

Chemical Property of (1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester

There total 7 articles about (1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl 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:

5-methoxynaphthalen-1-ol (3588-80-5) → (1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester (78176-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / NaH / dimethylformamide

2: 1)t-butyllithium / 1) DME, -25 deg C 2) -25 deg C

3: hydrogen, KOH / 5percent Pd/C / 1.) AcOH, MeOH, 50 psi, 25 deg C, 4 h 2.)MeOH, 50 psi, 25 deg C, 30 h

With potassium hydroxide; hydrogen; tert.-butyl lithium; sodium hydride; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(81)80003-2

Reference yield:

1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate (93603-11-3) → (1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester (78176-53-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / I₂, KI; NaHCO₃

2: 97 percent / tri-n-butyltin hydride

3: 1)t-butyllithium / 1) DME, -25 deg C 2) -25 deg C

4: hydrogen, KOH / 5percent Pd/C / 1.) AcOH, MeOH, 50 psi, 25 deg C, 4 h 2.)MeOH, 50 psi, 25 deg C, 30 h

With potassium hydroxide; hydrogen; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium iodide; palladium on activated charcoal;

DOI:10.1016/0040-4039(81)80003-2

Reference yield:

(1S,2R,5S)-7-Oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester (7771-14-4,19903-11-8,74320-46-0,78176-49-5,188796-05-6) → (1S,2R,4R)-4-Hydroxy-2-(5-methoxy-1-methoxymethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester (78176-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1)t-butyllithium / 1) DME, -25 deg C 2) -25 deg C

2: hydrogen, KOH / 5percent Pd/C / 1.) AcOH, MeOH, 50 psi, 25 deg C, 4 h 2.)MeOH, 50 psi, 25 deg C, 30 h

With potassium hydroxide; hydrogen; tert.-butyl lithium; palladium on activated charcoal;

DOI:10.1016/0040-4039(81)80003-2

upstream raw materials:

diazomethane

5-methoxynaphthalen-1-ol

1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate

(1S,2R,5S)-7-Oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Downstream raw materials:

4-Hydroxy-2-(1,4,5-trimethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester

4-Hydroxy-2-(1,4,5-trimethoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid

4-Hydroxy-2-(5-methoxy-1,4-dioxo-1,4-dihydro-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester

4-Hydroxy-2-(1-hydroxy-5-methoxy-naphthalen-2-ylmethyl)-cyclohexanecarboxylic acid methyl ester