dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate

Base Information

• Chemical Name: dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate
• CAS No.: 753020-09-6
• Molecular Formula: C₄₉H₆₄NO₅P
• Molecular Weight: 778.025
• Mol file: 753020-09-6.mol

Synonyms:dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate

Chemical Property of dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate

There total 14 articles about dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate 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:

tetramethyl methylenediphosphonate (16001-93-7) + (2R,3S,4S)-3,4-Bis-benzyloxy-2-dibenzylamino-octadec-5-ynal (1053626-17-7) → dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate (753020-09-6)

Guidance literature:

tetramethyl methylenediphosphonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

(2R,3S,4S)-3,4-Bis-benzyloxy-2-dibenzylamino-octadec-5-ynal; In tetrahydrofuran; for 2h;

DOI:10.1021/jo0493065

Reference yield:

(2R,3R)-3-(benzyloxy)butane-1,2,4-triol (84379-52-2) → dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate (753020-09-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 91 percent / camphorsulfonic acid / tetrahydrofuran / 2 h / Heating

2.1: pyridinium chlorochroamte; sodium acetate / CH₂Cl₂ / 4 h / 20 °C

3.1: n-BuLi / diethyl ether; hexane / 1 h / -20 °C

3.2: 70 percent / diethyl ether; hexane / -20 - 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: 82 percent / L-Selectride / tetrahydrofuran / 1 h / -78 - 20 °C

6.1: NaH; TBAB / tetrahydrofuran / 3 h / Heating

7.1: 1.46 g / H₂SO₄ / methanol; H₂O / 20 °C

8.1: PPh₃; DIAD / CH₂Cl₂ / 3 h / 0 °C

8.2: Me₃SiN₃ / CH₂Cl₂ / 0 - 20 °C

8.3: 61 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

9.1: PPh₃ / tetrahydrofuran; H₂O / 48 h / 20 °C

10.1: 0.99 g / K₂CO₃; NaOH / H₂O / 2 h / Heating

11.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

12.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

12.2: 318 mg / tetrahydrofuran / 2 h

With sodium hydroxide; n-butyllithium; di-isopropyl azodicarboxylate; sulfuric acid; camphor-10-sulfonic acid; tetrabutylammomium bromide; sodium acetate; L-Selectride; sodium hydride; potassium carbonate; Dess-Martin periodane; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 4.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation / 12.1: Horner-Wadsworth-Emmons reaction / 12.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo0493065

Reference yield:

(4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate (91326-83-9) → dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate (753020-09-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 80 percent / LiAlH₄; AlCl₃ / diethyl ether / 2 h / Heating

2.1: 91 percent / camphorsulfonic acid / tetrahydrofuran / 2 h / Heating

3.1: pyridinium chlorochroamte; sodium acetate / CH₂Cl₂ / 4 h / 20 °C

4.1: n-BuLi / diethyl ether; hexane / 1 h / -20 °C

4.2: 70 percent / diethyl ether; hexane / -20 - 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: 82 percent / L-Selectride / tetrahydrofuran / 1 h / -78 - 20 °C

7.1: NaH; TBAB / tetrahydrofuran / 3 h / Heating

8.1: 1.46 g / H₂SO₄ / methanol; H₂O / 20 °C

9.1: PPh₃; DIAD / CH₂Cl₂ / 3 h / 0 °C

9.2: Me₃SiN₃ / CH₂Cl₂ / 0 - 20 °C

9.3: 61 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

10.1: PPh₃ / tetrahydrofuran; H₂O / 48 h / 20 °C

11.1: 0.99 g / K₂CO₃; NaOH / H₂O / 2 h / Heating

12.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

13.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

13.2: 318 mg / tetrahydrofuran / 2 h

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; di-isopropyl azodicarboxylate; sulfuric acid; camphor-10-sulfonic acid; tetrabutylammomium bromide; sodium acetate; L-Selectride; sodium hydride; potassium carbonate; Dess-Martin periodane; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 5.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation / 13.1: Horner-Wadsworth-Emmons reaction / 13.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo0493065

upstream raw materials:

tetramethyl methylenediphosphonate

(2R,3S,4S)-3,4-Bis-benzyloxy-2-dibenzylamino-octadec-5-ynal

benzyl bromide

(2R,3R)-3-(benzyloxy)butane-1,2,4-triol

Downstream raw materials:

(3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonic acid