(3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene

Base Information

• Chemical Name: (3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene
• CAS No.: 128684-79-7
• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.364
• Mol file: 128684-79-7.mol

Synonyms:(3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene

Chemical Property of (3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene

There total 6 articles about (3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene 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%

(3S,4S)-4-carbomethoxy-3-hydroxy-1-<(4-methoxybenzyl)oxy>hept-6-ene (118207-49-1) → (3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene (128684-79-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; 1.) 0 deg C, 3 h, 2.) RT, 1 h;

DOI:10.1021/ja00170a024

Reference yield: 82.0%

ethyl (S)-2-((S)-1-hydroxy-3-((4-methoxybenzyl)oxy)propyl)pent-4-enoate → (3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene (128684-79-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -78 - 20 ℃; for 3.25h; Inert atmosphere;

DOI:10.1002/anie.201908917

Reference yield:

5-(4-methoxybenzyloxy)-3-oxopentanoic acid methyl ester (118207-58-2) → (3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene (128684-79-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / H₂, Et₃N / 1percent Ru₂Cl₄<(S)-binap>2

2: 1.) LDA / 1.) THF, Et₂O, HMPA

3: 86 percent / LiAlH₄

With lithium aluminium tetrahydride; hydrogen; triethylamine; lithium diisopropyl amide; Ru₂Cl₄((S)-BINAP)2;

DOI:10.1021/jo00262a008

upstream raw materials:

(3S,4S)-4-carbomethoxy-3-hydroxy-1-<(4-methoxybenzyl)oxy>hept-6-ene

methyl (3S)-3-hydroxy-5-<(4-methoxybenzyl)oxy>pentanoate

5-(4-methoxybenzyloxy)-3-oxopentanoic acid methyl ester

3-(p-methoxybenzyloxy)propanal

Downstream raw materials:

<2R,2(2S,4S)>-2-<2-(4-methoxyphenyl)-1,3-dioxan-1-yl>pent-4-en-1-ol

<3S,3(2RS,4R)>-3-<(4-methoxybenzyl)oxy>-3-<2-(iodomethyl)tetrahydrofuran-4-yl>propan-1-ol

<3S,3(4R)>-3-<(4-methoxybenzyl)oxy>-3-<2-(iodomethyl)tetrahydrofuran-4-yl>propanal

<3S,4S,6S,6(4R)>-4-hydroxy-6-<(4-methoxybenzyl)oxy>-3-methyl-6-<2-(iodomethyl)tetrahydrofuran-4-yl>hex-1-ene