8-[(S)-Hydroxy[4-benzyloxyphenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester

Base Information

• Chemical Name: 8-[(S)-Hydroxy[4-benzyloxyphenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester
• CAS No.: 182227-19-6
• Molecular Formula: C₂₅H₃₀O₆
• Molecular Weight: 426.51
• DSSTox Substance ID: DTXSID40441276
• Wikidata: Q82257986
• Mol file: 182227-19-6.mol

Synonyms:182227-19-6;ethyl 8-[(S)-hydroxy-(4-phenylmethoxyphenyl)methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylate;8-[(S)-Hydroxy[4-benzyloxyphenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester;FT-0669421;DTXSID40441276;LHQREPLLEPMRRW-QFIPXVFZSA-N

Chemical Property of 8-[(S)-Hydroxy[4-benzyloxyphenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester

Chemical Property:

• PSA: 74.22000
• LogP: 4.16560
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 426.20423867
• Heavy Atom Count: 31
• Complexity: 563

Purity/Quality:

98% ^*data from raw suppliers

8-[(S)-Hydroxy[4-benzyloxyphenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1(CCC2(CC1)OCCO2)C(C3=CC=C(C=C3)OCC4=CC=CC=C4)O
• Isomeric SMILES: CCOC(=O)C1(CCC2(CC1)OCCO2)[C@H](C3=CC=C(C=C3)OCC4=CC=CC=C4)O
• Uses: Intermediate in the synthesis of a cholesterol absorption inhibitor.

Technology Process of 8-[(S)-Hydroxy[4-benzyloxyphenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester

There total 4 articles about 8-[(S)-Hydroxy[4-benzyloxyphenyl]methyl]-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid Ethyl Ester 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:

8-[(S)-(4-Benzyloxy-phenyl)-trimethylsilanyloxy-methyl]-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester → 8-[(S)-(4-Benzyloxy-phenyl)-hydroxy-methyl]-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (182227-19-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Yield given; Ambient temperature;

DOI:10.1021/jo9704366

Reference yield:

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (1489-97-0) → 8-[(S)-(4-Benzyloxy-phenyl)-hydroxy-methyl]-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (182227-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA / 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C, 30 min, -20 deg C --> rt, 1 h

2: N-(2-naphthalenesulfonyl)-D-valine, BH₃*THF / various solvent(s) / 3 h / -78 °C

3: n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

With borane-THF; tetrabutyl ammonium fluoride; N-(2-naphthalenesulfonyl)-D-valine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo9704366

Reference yield:

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → 8-[(S)-(4-Benzyloxy-phenyl)-hydroxy-methyl]-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (182227-19-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / 4-MeC₆H₄SO₃H / Heating

2: 1.) LDA / 1) THF, -20 deg C, 1 h, 2) THF, -20 deg C, 30 min, -20 deg C --> rt, 1 h

3: N-(2-naphthalenesulfonyl)-D-valine, BH₃*THF / various solvent(s) / 3 h / -78 °C

4: n-Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

With borane-THF; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; N-(2-naphthalenesulfonyl)-D-valine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo9704366

upstream raw materials:

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate

ethyl 4-oxocyclohexane-1-carboxylate

[(1,4-Dioxa-spiro[4.5]dec-8-ylidene)-ethoxy-methoxy]-trimethyl-silane

Downstream raw materials:

(R)-3-(4-Benzyloxy-phenyl)-7-(4-chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-2-aza-spiro[3.5]nonan-1-one

(R)-7-(4-Chloro-phenyl)-2-(4-fluoro-phenyl)-7-hydroxy-3-(4-hydroxy-phenyl)-2-aza-spiro[3.5]nonan-1-one

(+)-(R)-2-(4-fluorophenyl)-3-(4-(benzyloxy)phenyl)-2-azaspiro[3.5]nonane-1,7-dione

1-[(S)-(4-Benzyloxy-phenyl)-hydroxy-methyl]-4-oxo-cyclohexanecarboxylic acid (4-fluoro-phenyl)-amide

Refernces