methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate

Base Information

• Chemical Name: methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate
• CAS No.: 158195-46-1
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.224
• Mol file: 158195-46-1.mol

Synonyms:methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate

Chemical Property of methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate

There total 6 articles about methyl (1S,2S,3R)-3-hydroxy-2-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: 70.0%

methanol (67-56-1) + (1S,5R,8S)-8-Methoxy-6-oxa-bicyclo[3.2.1]octan-7-one (158195-45-0) → methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate (158195-46-1)

Guidance literature:

With potassium carbonate; a) 0 deg C, 24 h, b) RT, 4 h;

DOI:10.1080/00397919408019060

Reference yield: 25.0%

methanol (67-56-1) + (1S,5R,8S)-8-Methoxy-6-oxa-bicyclo[3.2.1]octan-7-one (158195-45-0) → methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate (158195-46-1) + (1R,2S,3R)-3-Hydroxy-2-methoxy-cyclohexanecarboxylic acid methyl ester

Guidance literature:

With potassium carbonate;

DOI:10.1016/0957-4166(94)80007-3 DOI:10.1021/jo951693i

Reference yield:

(1S,2R)-2-methoxy-3-cyclohexenyl-1-carboxylic acid (158252-23-4) → methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate (158195-46-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / NaHCO₃, KI, I₂ / H₂O

2: 99 percent / Bu₃SnH, AIBN / benzene

3: 70 percent / K₂CO₃

With 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium carbonate; potassium iodide; In water; benzene;

DOI:10.1021/jo951693i

upstream raw materials:

methanol

(1S,5R,8S)-8-Methoxy-6-oxa-bicyclo[3.2.1]octan-7-one

(1S,2R)-2-methoxy-3-cyclohexenyl-1-carboxylic acid

(1S,4S,5S,8S)-4-Iodo-8-methoxy-6-oxa-bicyclo[3.2.1]octan-7-one

Downstream raw materials:

methyl (1S,2S,3R)-3-mesyloxy-2-methoxy-1-cyclohexanecarboxylate

methyl (1S,2S)-2-methoxy-3-oxo-1-cyclohexane carboxylate

methyl (1S,2S)-3-(N-hydroxylamino)-2-methoxycyclohexane carboxylate