(2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol

Base Information

• Chemical Name: (2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol
• CAS No.: 202464-95-7
• Molecular Formula: C₂₈H₄₄O₄
• Molecular Weight: 444.655
• Mol file: 202464-95-7.mol

Synonyms:(2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol

Chemical Property of (2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol

There total 9 articles about (2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol 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: 85.0%

benzoyl cyanide (613-90-1) + (2R,3R,4E)-1,2-O-isopropylidene-3-hydroxy-4-octadecene-1,2-diol (121998-82-1) → (2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol (202464-95-7)

Guidance literature:

With triethylamine; In dichloromethane; 1.) 0 deg C, 2 h, 2.) r.t., 4 h;

DOI:10.1055/s-1998-4482

Reference yield: 76.6%

benzoyl chloride (98-88-4) + (2R,3R,4E)-1,2-O-isopropylidene-3-hydroxy-4-octadecene-1,2-diol (121998-82-1) → (2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol (202464-95-7)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.bmc.2014.08.002

Reference yield:

2,3,4,5-di-O-isopropylidene-D-xylose aldehyde (13039-94-6) → (2R,3R,4E)-3-benzoyloxy-1,2-O-isopropylideneoctadec-4-ene-1,2-diol (202464-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / methanol / 4 h / Ambient temperature

2: 48 percent / diethyl ether / 1.) 0 deg C, 0.5 h, 2.) r.t., overnight

3: 85 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) r.t., 4 h

With triethylamine; In methanol; diethyl ether; dichloromethane;

DOI:10.1055/s-1998-4482

upstream raw materials:

benzoyl cyanide

(2R,3R,4E)-1,2-O-isopropylidene-3-hydroxy-4-octadecene-1,2-diol

benzoyl chloride

myristylaldehyde

Downstream raw materials:

(2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol

(2S,3R,4E)-2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol

(2S,3R,4E)-2-azido-1-benzoyloxy-octadec-4-ene-3-ol

(2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol