3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoic acid

Base Information

• Chemical Name: 3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoic acid
• CAS No.: 1472660-04-0
• Molecular Formula: C₁₁H₁₈O₄
• Molecular Weight: 214.262
• Mol file: 1472660-04-0.mol

Synonyms:

Chemical Property of 3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoic acid

There total 2 articles about 3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoic acid 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: 91.0%

(S)-ethyl 3-(1,4-dioxaspiro[4.5]decan-2-yl)propanoate (726193-03-9) → 3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoic acid (1472660-04-0)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; methanol; for 10h;

DOI:10.1002/hlca.201200519

Reference yield:

(E)-(S)-3-(1,4-Dioxa-spiro[4.5]dec-2-yl)-acrylic acid ethyl ester → 3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoic acid (1472660-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

2: water; lithium hydroxide / methanol; tetrahydrofuran / 10 h

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; water; lithium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1002/hlca.201200519

Reference yield:

3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoic acid (1472660-04-0) → C8Co2O8*C35H45NO4

Guidance literature:

Multi-step reaction with 16 steps

1.1: triethylamine / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

2.1: lithium chloride / tetrahydrofuran / 5 h / -20 - 0 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 °C / Inert atmosphere

4.1: lithium borohydride / methanol; tetrahydrofuran; diethyl ether / 1 h / -10 °C / Inert atmosphere

5.1: pyridine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

6.1: Dowex 50WX₈ / methanol / 48 h / 20 °C / Inert atmosphere

7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.67 h / 0 - 20 °C / Inert atmosphere

7.2: 0.5 h / 0 - 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

8.2: 0.67 h / -78 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.67 h / -78 °C / Inert atmosphere

10.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 3 h / 20 °C

11.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

12.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

12.2: 5 h / -78 - 0 °C / Inert atmosphere

13.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

14.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere

15.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 0 - 20 °C / Inert atmosphere

16.1: toluene / 0.5 h / 20 °C / Inert atmosphere

With pyridine; dmap; lithium borohydride; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; mineral oil; 12.1: |Wittig Olefination / 12.2: |Wittig Olefination;

DOI:10.1002/hlca.201200519

upstream raw materials:

(S)-ethyl 3-(1,4-dioxaspiro[4.5]decan-2-yl)propanoate

Downstream raw materials:

(2R,4S)-8-(benzyloxy)-2-methyloct-6-yne-1,4-diol

(3R,5S)-5-[4-(benzyloxy)but-2-yn-1-yl]-3-methyldihydrofuran-2(3H)-one

(3R,5S)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-ol

(4R)-4-benzyl-3-{3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]propanoyl}-1,3-oxazolidin-2-one