(2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide

Base Information

• Chemical Name: (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide
• CAS No.: 111194-09-3
• Molecular Formula: C₃₄H₃₄O₇
• Molecular Weight: 554.64

Synonyms:(2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide

Chemical Property of (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide

There total 2 articles about (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide 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: 88.0%

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) + (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone (111266-03-6) → (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide (111194-09-3)

Guidance literature:

(R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -70 ℃; for 0.25h;

3-methoxy-4-(phenylmethoxy)benzaldehyde; In tetrahydrofuran; toluene; at -70 ℃; for 2h; Further stages.;

DOI:10.1021/np050089s

Reference yield: 41.0%

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) + (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone (111266-03-6) → (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide (111194-09-3) + (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(R)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide (111266-04-7)

Guidance literature:

(R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone; With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃; for 0.5h;

3-methoxy-4-(phenylmethoxy)benzaldehyde; In tetrahydrofuran; at -70 ℃; for 1h; Further stages.;

DOI:10.1021/np050089s

Reference yield: 87.0%

(2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide (111194-09-3) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide (868127-86-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/np050089s

upstream raw materials:

3-methoxy-4-(phenylmethoxy)benzaldehyde

(R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone

Downstream raw materials:

matairesinol

(2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide

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