(5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate

Base Information

• Chemical Name: (5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate
• CAS No.: 1609262-98-7
• Molecular Formula: C₂₃H₃₃NO₆
• Molecular Weight: 419.518
• Mol file: 1609262-98-7.mol

Synonyms:(5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate

Chemical Property of (5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate

There total 11 articles about (5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate 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: 90.0%

(5S,6R)-erythro-6-hydroxy-5-hexadecanolide (96720-02-4) + 4-nitro-benzoic acid (62-23-7) → (5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate (1609262-98-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.03.006

Reference yield:

2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran (1720-37-2) → (5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate (1609262-98-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 - -20 °C

1.2: -78 - 20 °C

2.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran; diethylene glycol dimethyl ether / 13 h / 0 - 160 °C

4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

5.1: sulfuric acid / 5 h / 78 °C

6.1: methanesulfonamide; AD-mix β / water; tert-butyl alcohol / 60 h / 0 °C

7.1: sodium hydroxide / water / 2 h / 60 °C

7.2: 20 °C

8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; methanesulfonamide; AD-mix β; sulfuric acid; toluene-4-sulfonic acid; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; diethylene glycol dimethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: |Sharpless Dihydroxylation / 8.1: |Mitsunobu Displacement;

DOI:10.1016/j.tetasy.2014.03.006

Reference yield:

hexadec-5-yn-1-ol (72443-47-1) → (5R,6S)-6-hydroxy-5-hexadecanolide-4-nitrobenzoate (1609262-98-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethylene glycol dimethyl ether / 13 h / 0 - 160 °C

2.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: sulfuric acid / 5 h / 78 °C

4.1: methanesulfonamide; AD-mix β / water; tert-butyl alcohol / 60 h / 0 °C

5.1: sodium hydroxide / water / 2 h / 60 °C

5.2: 20 °C

6.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; dipyridinium dichromate; methanesulfonamide; AD-mix β; sulfuric acid; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; diethylene glycol dimethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: |Sharpless Dihydroxylation / 6.1: |Mitsunobu Displacement;

DOI:10.1016/j.tetasy.2014.03.006

upstream raw materials:

2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran

Iododecane

1-bromo dodecane

hexadec-5-yn-1-ol

Downstream raw materials:

(5R,6S)-6-hydroxyhexadecan-5-olide

Refernces