(2R,3S,4R)-2-Benzyloxy-4-methyl-hex-5-en-3-ol

Base Information

• Chemical Name: (2R,3S,4R)-2-Benzyloxy-4-methyl-hex-5-en-3-ol
• CAS No.: 124377-77-1
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.312
• Mol file: 124377-77-1.mol

Synonyms:

Chemical Property of (2R,3S,4R)-2-Benzyloxy-4-methyl-hex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-2-Benzyloxy-4-methyl-hex-5-en-3-ol

There total 3 articles about (2R,3S,4R)-2-Benzyloxy-4-methyl-hex-5-en-3-ol 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: 31.0%

2-(benzyloxy)propanal (53346-05-7) + crotylmagnesium chloride (21969-32-4) → (2R*,3R*,4R*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (124377-78-2) + (2R*,3R*,4S*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (124377-76-0) + (2R*,3S*,4R*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (124377-77-1) + (2R*,3S*,4S*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (124377-75-9)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃; for 1h; Product distribution; other α-alkoxy aldehyde, other crotyl organometallics, var. temp. and time;

DOI:10.1021/jo00287a032

Reference yield:

2-(benzyloxy)propanal (53346-05-7) + tri-n-butylcrotyltin (35998-93-7) → (2R*,3S*,4R*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (124377-77-1) + (2R*,3S*,4S*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (124377-75-9)

Guidance literature:

With magnesium bromide; In dichloromethane; react. of Sn-compd. (90 % E) with propanal in presence of MgBr2 in CH2Cl2 at -25°C; total yield 80 %, ratio erythro/threo = 90/10;

DOI:10.1039/c39900001161

Reference yield:

2-(benzyloxy)propanal (53346-05-7) + tri-n-butylcrotyltin (35998-93-7) + (Z)-crotyltri-n-butylstannane (35998-94-8) → (2R*,3S*,4R*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (124377-77-1) + (2R*,3S*,4S*)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (124377-75-9)

Guidance literature:

With magnesium bromide; In dichloromethane; react. of Sn-compd. (E/Z = 56/44) with propanal in presence of MgBr2 in CH2Cl2 at -78°C; ratio erythro/threo = 93/7;

DOI:10.1039/c39900001161

upstream raw materials:

2-(benzyloxy)propanal

crotylmagnesium chloride

tri-n-butylcrotyltin

(Z)-crotyltri-n-butylstannane

Downstream raw materials:

(3R,4R,5S)-5-((S)-1-Benzyloxy-ethyl)-4-methyl-tetrahydro-furan-3-ol