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

Base Information

• Chemical Name: ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol
• CAS No.: 1425631-48-6
• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.37
• Mol file: 1425631-48-6.mol

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

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

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)methanol

There total 3 articles about ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol 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: 93.0%

(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)methanol (1425631-48-6)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

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)methanol (1425631-48-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/ol400228v

Reference yield:

orthoformic acid triethyl ester (122-51-0) → ((3S,4S)-3-(diethoxymethyl)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol (1425631-48-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-butyldimethylsiyl triflate; triethylamine / dichloromethane / 0.42 h / 0 - 23 °C / Inert atmosphere

1.2: 0.42 h / 0 °C / Inert atmosphere

2.1: sodium tetrahydroborate; ethanol / dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere

With sodium tetrahydroborate; ethanol; t-butyldimethylsiyl triflate; triethylamine; In dichloromethane; 1.2: |Mukaiyama Aldol Addition;

DOI:10.1021/jacs.1c00557

upstream raw materials:

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

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

orthoformic acid triethyl ester

Downstream raw materials:

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