(1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate

Base Information

• Chemical Name: (1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate
• CAS No.: 1313587-34-6
• Molecular Formula: C₂₇H₄₂O₆
• Molecular Weight: 462.627

Synonyms:(1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate

Chemical Property of (1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate

There total 6 articles about (1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate 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%

(1Z,2S,3R,4S,6S,7R)-1-ethylidene-7-hydroxy-2,4,6-trimethyl-5-oxo-3-[(1S)-1-phenylethoxy]octyl isobutyrate (1313587-28-8) + acetaldehyde (75-07-0,9002-91-9) → (1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate (1313587-34-6)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at -20 ℃; for 18h; Inert atmosphere; Darkness;

DOI:10.1002/ejoc.201100196

Reference yield:

(1Z,2S,3R,4S,6S,7R)-1-ethylidene-7-hydroxy-2,4,6-trimethyl-5-oxo-3-[(1S)-1-phenylethoxy]octyl isobutyrate (1313587-28-8) + acetaldehyde (75-07-0,9002-91-9) → (1Z,2S,3S,4R,5S,6R,7R)-7-acetoxy-1-ethylidene-5-hydroxy-2,4,6-trimethyl-3-[(1S)-1-phenylethoxy]octyl isobutyrate (1313587-33-5) + (1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate (1313587-34-6)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at -20 ℃; for 4h; Inert atmosphere; Darkness;

DOI:10.1002/ejoc.201100196

Reference yield:

C29H48O4Si → (1Z,2S,3S,4S,5R,6S,7R)-7-acetoxy-1-ethylidene-3-hydroxy-2,4,6-trimethyl-5-[(1S)-1-phenylethoxy]octyl isobutyrate (1313587-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / -78 °C / Inert atmosphere

2: samarium diiodide / tetrahydrofuran / 18 h / -20 °C / Inert atmosphere; Darkness

With samarium diiodide; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; 2: Evans-Tishchenko reduction;

DOI:10.1002/ejoc.201100196

upstream raw materials:

(1Z,2S,3R,4S,6S,7R)-1-ethylidene-7-hydroxy-2,4,6-trimethyl-5-oxo-3-[(1S)-1-phenylethoxy]octyl isobutyrate

acetaldehyde

(-)-(1Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate

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