(2R,3R)-diethyl 1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate

Base Information

• Chemical Name: (2R,3R)-diethyl 1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate
• CAS No.: 61045-33-8
• Molecular Formula: C14H22O6
• Molecular Weight: 286.32100
• Mol file: 61045-33-8.mol

Synonyms:O,O'-Cyclohexyliden-Lg-weinsaeure-diaethylester;O,O'-cyclohexylidene-Lg-tartaric acid diethyl ester;(2R,3R)-1,4-Dioxa-spiro[4.5]decane-2,3-dicarboxylic acid diethyl ester;(2R,3R)-diethyl 1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate;

Chemical Property of (2R,3R)-diethyl 1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate

Chemical Property:

• Boiling Point: 125 - 140 °C (0.5 mmHg)
• PSA: 71.06000
• LogP: 1.55700

Purity/Quality:

>95%,>98%e.e. ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3R)-diethyl 1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate

There total 4 articles about (2R,3R)-diethyl 1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate 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%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + L-(+)-diethyl tartrate → diethyl (2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate (61045-33-8,93922-63-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 24h; Heating;

Reference yield: 66.0%

diethyl (2R,3R)-tartrate (87-91-2) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → diethyl (2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate (61045-33-8,93922-63-5)

Guidance literature:

Amberlyst 15 ion-exchange resin; In toluene; for 12h; Heating / reflux;

Reference yield: 61.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + Diethyl L-tartrate (68631-50-5) → diethyl (2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate (61045-33-8,93922-63-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 16h; Heating;

DOI:10.1021/jo00200a027

upstream raw materials:

diethyl (2R,3R)-tartrate

cyclohexanone

Diethyl L-tartrate

Downstream raw materials:

(4R,5S)-3-{(2S,3R)-2-[(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1,4-dioxa-spiro[4.5]dec-2-yl]-5-oxo-tetrahydro-furan-3-yl}-4,5-diphenyl-oxazolidin-2-one

(3R,4S)-4-[(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1,4-dioxa-spiro[4.5]dec-2-yl]-4-hydroxy-3-((4R,5S)-2-oxo-4,5-diphenyl-oxazolidin-3-yl)-butyric acid

(4R,5S)-3-((R)-1-{(S)-[(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1,4-dioxa-spiro[4.5]dec-2-yl]-hydroxy-methyl}-3-trimethylsilanyl-prop-2-ynyl)-4,5-diphenyl-oxazolidin-2-one

Dibenzyl-{(2S,3S)-3-[(dibenzylamino)-methyl]-1,4-dioxa-spiro[4.5]dec-2-ylmethyl}-amine

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