(2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile

Base Information

• Chemical Name: (2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile
• CAS No.: 1609533-98-3
• Molecular Formula: C₂₆H₃₅NO₃
• Molecular Weight: 409.569
• Mol file: 1609533-98-3.mol

Synonyms:(2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile

Chemical Property of (2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile

There total 2 articles about (2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile 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: 90.0%

(2R,3S)-3-(benzyloxy)hept-6-ene-1,2-diol (1554519-04-8) + [(E)-1-Cyano-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyl]-phosphonic acid diethyl ester (202338-89-4) → (2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile (1609533-98-3)

Guidance literature:

(2R,3S)-3-(benzyloxy)hept-6-ene-1,2-diol; With sodium periodate; In water; acetonitrile; at 0 ℃; for 2h;

[(E)-1-Cyano-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyl]-phosphonic acid diethyl ester; With potassium hexamethylsilazane; In toluene; at -78 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.04.018

Reference yield:

(S)-1-((R)-1,4-dioxaspiro[4.5]decan-2-yl)pent-4-en-1-ol (113730-85-1) → (2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile (1609533-98-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 20 °C

2.1: hydrogenchloride / methanol; water / 15 h / 40 °C

3.1: sodium periodate / water; acetonitrile / 2 h / 0 °C

3.2: 0.17 h / -78 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; sodium hydride; In methanol; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1016/j.tetlet.2014.04.018

Reference yield: 89.0%

(2Z)-(4S)-4-benzyloxy-2-[(E)-4-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-enyl]octa-2,7-dienenitrile (1609533-98-3) → (2Z)-(4S)-4-benzyloxy-2-[(E)-5-hydroxy-4-methylpent-3-enyl]octa-2,7-dienenitrile (1609533-99-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 13h;

DOI:10.1016/j.tetlet.2014.04.018

upstream raw materials:

(S)-1-((R)-1,4-dioxaspiro[4.5]decan-2-yl)pent-4-en-1-ol

(2R,3S)-3-(benzyloxy)hept-6-ene-1,2-diol

[(E)-1-Cyano-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyl]-phosphonic acid diethyl ester

Downstream raw materials:

ethyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate

methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate

(4aR,4bR,5S,8aS)-5-benzyloxy-4a-methyl-8-methylene-2-oxo-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthrene-8a-carbonitrile

(1S,4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-4a-methyl-8-methylene-2-oxoperhydro-phenanthrene-8a-carbonitrile