5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone

Base Information

Chemical Name:5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone
CAS No.:745073-47-6
Molecular Formula:C₂₉H₄₄O₆
Molecular Weight:488.665
Hs Code.:

Synonyms:5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone

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Chemical Property of 5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone

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Technology Process of 5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone

There total 7 articles about 5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone 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:

: 745073-40-9
5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-(4-methoxyphenoxy)methyltetrahydro-2-furanone

: 745073-47-6
5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone

Guidance literature:: With ammonium cerium(IV) nitrate; In acetonitrile; at 0 ℃; for 0.5h;
DOI:10.1021/jm0497747

Reference yield:

: 7735-42-4
1,16-hexadecanediol

: 745073-47-6
5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine / dimethylformamide / 1 h / 20 °C

2.1: pyridinium chloroformate; molecular sieves 4A / CH₂Cl₂ / 1 h / 20 °C

3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 2 h / -78 °C

4.1: Et₃N; MeSO₂Cl / CH₂Cl₂ / 2.5 h / 0 - 20 °C

4.2: diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.5 h / 0 °C

5.1: HCO₂H / diethyl ether / 1 h / 20 °C

6.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C

7.1: aq. ammonium cerium nitrate / acetonitrile / 0.5 h / 0 °C

With pyridine; dipyridinium dichromate; formic acid; ammonium cerium(IV) nitrate; pyridinium chloroformate; 4 A molecular sieve; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0497747

Reference yield:

: 745073-20-5
16-(trityloxy)-1-hexadecanal

: 745073-47-6
5-(benzyloxy)methyl-3-[(Z)-16-carboxypentadecylidene]-5-hydroxymethyltetrahydro-2-furanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 2 h / -78 °C

2.1: Et₃N; MeSO₂Cl / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2.2: diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.5 h / 0 °C

3.1: HCO₂H / diethyl ether / 1 h / 20 °C

4.1: pyridinium dichromate / dimethylformamide / 24 h / 20 °C

5.1: aq. ammonium cerium nitrate / acetonitrile / 0.5 h / 0 °C

With dipyridinium dichromate; formic acid; ammonium cerium(IV) nitrate; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0497747