(2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol

Base Information

• Chemical Name: (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol
• CAS No.: 753020-04-1
• Molecular Formula: C₃₀H₄₆O₄
• Molecular Weight: 470.693
• Mol file: 753020-04-1.mol

Synonyms:(2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol

Chemical Property of (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol

There total 8 articles about (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-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-O-benzyl-1,2-O-(3'-pentylidene)-5-octadecyn-1,2,3,4-tetrol (753020-03-0) → (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol (753020-04-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo0493065

Reference yield:

(2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-5-octadecyn-1,2,3,4-tetrol (753020-03-0) → (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol (753020-04-1) + (2R,3S)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1021/jo0493065

Reference yield:

(2R,3R)-3-(benzyloxy)butane-1,2,4-triol (84379-52-2) → (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol (753020-04-1)

Guidance literature:

Multi-step reaction with 4 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

With n-butyllithium; camphor-10-sulfonic acid; sodium acetate; Dess-Martin periodane; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 4.1: Dess-Martin oxidation;

DOI:10.1021/jo0493065

upstream raw materials:

(2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-5-octadecyn-1,2,3,4-tetrol

3,3-dimethoxypentane

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

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

Downstream raw materials:

(2R,3R,4S)-3-O-benzyl-1,2-O-(3'-pentylidene)-5-octadecyn-1,2,3,4-tetrol

(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

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