(2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol

Base Information

• Chemical Name: (2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol
• CAS No.: 109333-88-2
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.312
• Mol file: 109333-88-2.mol

Synonyms:(2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol

Chemical Property of (2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol

There total 4 articles about (2S,3S,4S)-2-(benzyloxy)-4-methylhex-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:

trans-2-Butene (624-64-6) + (S)-2-(benzyloxy)propanal (81445-44-5) → (2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol (109333-88-2)

Guidance literature:

trans-2-Butene; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -78 - -45 ℃; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Inert atmosphere;

(S)-2-(benzyloxy)propanal; optical yield given as %de; Further stages;

DOI:10.1021/ol800902g

Reference yield:

(S)-2-(benzyloxy)propanal (81445-44-5) + (Z)-crotyltrimethoxysilane (259150-83-9) → (2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol (109333-88-2) + (2S,3R,4R)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (109430-15-1) + (2S,3R,4S)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (109430-17-3)

Guidance literature:

(S)-2-(benzyloxy)propanal; (Z)-crotyltrimethoxysilane; With (IPr)CuF; n-octyltrifluorosilane; In tetrahydrofuran; at 20 ℃; for 48h; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; for 1h; Inert atmosphere;

DOI:10.1021/ol902458v

Reference yield:

(S)-2-(benzyloxy)propanal (81445-44-5) + B-crotyldiisopinocampheylborane (99493-12-6) → (2S,3S,4S)-2-(benzyloxy)-4-methylhex-5-en-3-ol (109333-88-2) + (2S,3R,4R)-2-(benzyloxy)-4-methyl-5-hexen-3-ol (109430-15-1)

Guidance literature:

In diethyl ether; at -78 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00268a017

upstream raw materials:

(S)-2-(benzyloxy)propanal

crotyltri-n-butylstannane

B-crotyldiisopinocampheylborane

trans-2-Butene

Downstream raw materials:

(5S,6S)-6-((S)-1-(benzyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-one