methyl (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate

Base Information

• Chemical Name: methyl (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate
• CAS No.: 618888-69-0
• Molecular Formula: C₁₁H₂₀O₇
• Molecular Weight: 264.276

Synonyms:methyl (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate

Chemical Property of methyl (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate

Chemical Property:

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Technology Process of methyl (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate

There total 2 articles about methyl (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-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: 83.0%

methanol (67-56-1) + (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-4-benzoyl-1-hydroxycyclohexane-1,3-carbolactone (618888-66-7) → methyl (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate (618888-69-0)

Guidance literature:

With sodium methylate; at 20 ℃; for 6h;

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-(2',3'-dihydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate (618888-69-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 22 percent / aq. OsO₄; N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C

2: 83 percent / NaOMe / 6 h / 20 °C

With osmium(VIII) oxide; sodium methylate; 4-methylmorpholine N-oxide; In acetone; tert-butyl alcohol;

DOI:10.1039/b301731a

Reference yield: 100.0%

methyl (1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate (618888-69-0) → (1S,3S,4R,5R)-3-(2,3-Dihydroxy-propyl)-1,4,5-trihydroxy-cyclohexanecarboxylic acid

Guidance literature:

With sodium hydroxide; at 20 ℃; pH=12;

DOI:10.1039/b301731a

upstream raw materials:

methanol

(1S,3R,4R,5S)-5-(2',3'-dihydroxypropyl)-4-benzoyl-1-hydroxycyclohexane-1,3-carbolactone

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

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