racemic threo 6-acetoxy-5-hexadecanolide

Base Information

Chemical Name:racemic threo 6-acetoxy-5-hexadecanolide
CAS No.:85551-40-2
Molecular Formula:C₁₈H₃₂O₄
Molecular Weight:312.45
Hs Code.:

Synonyms:

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Chemical Property of racemic threo 6-acetoxy-5-hexadecanolide

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Technology Process of racemic threo 6-acetoxy-5-hexadecanolide

There total 26 articles about racemic threo 6-acetoxy-5-hexadecanolide 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: 74.0%

: 108-24-7
acetic anhydride

: 89102-35-2,89102-36-3,96720-02-4,96720-03-5,107297-90-5,107297-91-6,109232-58-8,130550-75-3,130550-76-4
(5R*,6S*)-6-hydroxyhexadecan-5-olide

: 81792-36-1,85551-39-9,85551-40-2,85551-41-3,85551-42-4,97806-55-8,108102-45-0,118174-17-7,130550-77-5
racemic erythro 6-acetoxy-5-hexadecanolide

Guidance literature:: With pyridine; for 2.5h; Heating;

Reference yield:

: 108044-63-9,108044-64-0
Acetic acid (R)-(S)-1-(3,4-dihydro-2H-pyran-2-yl)-undecyl ester

: 81792-36-1,85551-39-9,85551-40-2,85551-41-3,85551-42-4,97806-55-8,108102-45-0,118174-17-7,130550-77-5
racemic erythro 6-acetoxy-5-hexadecanolide

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; at 25 ℃; for 5h;
DOI:10.1016/S0040-4039(00)84897-2

Reference yield:

: 693-67-4
bromoundecane

: 81792-36-1,85551-39-9,85551-40-2,85551-41-3,85551-42-4,97806-55-8,108102-45-0,118174-17-7,130550-77-5
racemic erythro 6-acetoxy-5-hexadecanolide

Guidance literature:: Multi-step reaction with 9 steps

1.1: acetonitrile

2.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

2.2: 82 percent / tetrahydrofuran / 2 h / -78 °C

3.1: aq. N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

4.1: p-TsOH / 0.5 h / 20 °C

5.1: 0.74 g / H₂ / 10 percent Pd/C / ethyl acetate / 0.5 h / 20 °C

6.1: 88 percent / PCC; Celite / CH₂Cl₂ / 2 h / 20 °C

7.1: NaIO₄; RuCl₃*H₂O / CCl₄; acetonitrile / 6 h

8.1: 2N aq. HCl / tetrahydrofuran / 16 h / Heating

9.1: 0.3 g / pyridine / 20 h / 20 °C

With pyridine; hydrogenchloride; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; n-butyllithium; Celite; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; acetonitrile; tert-butyl alcohol; 2.1: Wittig reaction;
DOI:10.1002/jccs.200100112