methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate

Base Information

• Chemical Name: methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate
• CAS No.: 618888-64-5
• Molecular Formula: C₁₁H₂₀O₆
• Molecular Weight: 248.276
• Mol file: 618888-64-5.mol

Synonyms:methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate

Chemical Property of methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate

There total 2 articles about methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate 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: 98.0%

methanol (67-56-1) + Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester (618888-62-3) → methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate (618888-64-5)

Guidance literature:

With sodium methylate; at 20 ℃; for 2h;

DOI:10.1039/b301731a

Reference yield:

(1S,3S,4R,5R)-3-allyl-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate (183474-89-7) → methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate (618888-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BH₃*THF / tetrahydrofuran / 1 h / 0 °C

1.2: 31 percent / aq. NaBO₃ / tetrahydrofuran / 2 h / 20 °C

2.1: 98 percent / NaOMe / 2 h / 20 °C

With borane-THF; sodium methylate; In tetrahydrofuran;

DOI:10.1039/b301731a

Reference yield: 65.0%

methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate (618888-64-5) → (1S,3R,4R,5S)-1,3,4-Trihydroxy-5-(3-hydroxy-propyl)-cyclohexanecarboxylic acid

Guidance literature:

With sodium hydroxide; at 20 ℃; for 2h; pH=12;

DOI:10.1039/b301731a

upstream raw materials:

methanol

Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester

(1S,3S,4R,5R)-3-allyl-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate