(2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol

Base Information

• Chemical Name: (2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol
• CAS No.: 753020-08-5
• Molecular Formula: C₄₆H₅₉NO₃
• Molecular Weight: 673.979
• Mol file: 753020-08-5.mol

Synonyms:(2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol

Chemical Property of (2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol

There total 12 articles about (2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol 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:

(2R,3R)-3-(benzyloxy)butane-1,2,4-triol (84379-52-2) → (2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol (753020-08-5)

Guidance literature:

Multi-step reaction with 10 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

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;

DOI:10.1021/jo0493065

Reference yield:

(4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate (91326-83-9) → (2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol (753020-08-5)

Guidance literature:

Multi-step reaction with 11 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

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;

DOI:10.1021/jo0493065

Reference yield:

(2R,3S)-2-O-benzyl-3,4-O-(3'-pentylidene)-2,3,4-trihydroxybutanal (753020-02-9) → (2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol (753020-08-5)

Guidance literature:

Multi-step reaction with 8 steps

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

1.2: 70 percent / diethyl ether; hexane / -20 - 20 °C

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

3.1: 82 percent / L-Selectride / tetrahydrofuran / 1 h / -78 - 20 °C

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

5.1: 1.46 g / H₂SO₄ / methanol; H₂O / 20 °C

6.1: PPh₃; DIAD / CH₂Cl₂ / 3 h / 0 °C

6.2: Me₃SiN₃ / CH₂Cl₂ / 0 - 20 °C

6.3: 61 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

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

8.1: 0.99 g / K₂CO₃; NaOH / H₂O / 2 h / Heating

With sodium hydroxide; n-butyllithium; di-isopropyl azodicarboxylate; sulfuric acid; tetrabutylammomium bromide; L-Selectride; sodium hydride; potassium carbonate; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 2.1: Dess-Martin oxidation;

DOI:10.1021/jo0493065

upstream raw materials:

benzyl bromide

(2S,3S,4S)-2-Amino-3,4-bis-benzyloxy-octadec-5-yn-1-ol

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

(4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate

Downstream raw materials:

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

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

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