(2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol

Base Information

• Chemical Name: (2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol
• CAS No.: 1448722-25-5
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.467
• Mol file: 1448722-25-5.mol

Synonyms:(2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol

Chemical Property of (2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol

There total 4 articles about (2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-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:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) + 2,4-O-benzylidene-D-threose (99274-32-5) → (2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol (1448722-25-5) + (2R,3R,4R,5S)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol (1448722-26-6)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; at 0 - 20 ℃; for 72h; Overall yield = 68 %; Overall yield = 216 mg; stereoselective reaction;

DOI:10.3987/COM-12-S(N)31

Reference yield:

(E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1057662-85-7) + 2,4-O-benzylidene-D-threose (99274-32-5) → (2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol (1448722-25-5) + (2R,3R,4R,5S)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol (1448722-26-6)

Guidance literature:

In dichloromethane; at -78 - 20 ℃; for 168h; Overall yield = 34 %; Overall yield = 14.8 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2016.07.030

Reference yield:

(Z)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1174918-98-9) + 2,4-O-benzylidene-D-threose (99274-32-5) → (2R,3R,4R,5R)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol (1448722-25-5) + (2R,3R,4R,5S)-1,3-[(S)-benzylidenedioxy]-5,9-dimethyl-5-vinyldec-8-ene-2,4-diol (1448722-26-6)

Guidance literature:

In dichloromethane; at -78 - 20 ℃; for 168h; Overall yield = 35 %; Overall yield = 14.8 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2016.07.030

upstream raw materials:

neryl chloride

2,4-O-benzylidene-D-threose

1-chloro-3,7-dimethylocta-2,6-diene

(E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane