((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate

Base Information

• Chemical Name: ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate
• CAS No.: 1425631-50-0
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• Mol file: 1425631-50-0.mol

Synonyms:((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate

Chemical Property of ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate

There total 4 articles about ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate 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: 91.0%

((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol (1425631-48-6) + ethyl propanoylacetate (4949-44-4) → ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate (1425631-50-0)

Guidance literature:

With dmap; In toluene; for 18h; Inert atmosphere; Reflux;

DOI:10.1021/ol400228v

Reference yield:

(S)-tert-butyldimethyl((4-(prop-1-en-2-yl)cyclohex-2-en-1-ylidene)methoxy)silane (498555-08-1) → ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate (1425631-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -78 °C

3: dmap / toluene / 18 h / Inert atmosphere; Reflux

With dmap; boron trifluoride diethyl etherate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; 1: |Mukaiyama Aldol Addition;

DOI:10.1021/ol400228v

Reference yield:

(3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-enecarbaldehyde (1425631-46-4) → ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl 3-oxopentanoate (1425631-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -78 °C

2: dmap / toluene / 18 h / Inert atmosphere; Reflux

With dmap; diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1021/ol400228v

upstream raw materials:

((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol

ethyl propanoylacetate

(S)-tert-butyldimethyl((4-(prop-1-en-2-yl)cyclohex-2-en-1-ylidene)methoxy)silane

(S)-(-)-perillaldehyde

Downstream raw materials:

1-((1S,2R,3S)-2-(diethoxymethyl)-6-methylene-3-(prop-1-en-2-yl)cyclohexyl)butan-2-one

1-((1R,2R,3S)-2-(diethoxymethyl)-6-methylene-3-(prop-1-en-2-yl)cyclohexyl)butan-2-one