Butanal, 4-methoxy-3-[(4-methoxyphenyl)methoxy]-, (3R)-

Base Information

• Chemical Name: Butanal, 4-methoxy-3-[(4-methoxyphenyl)methoxy]-, (3R)-
• CAS No.: 400737-27-1
• Molecular Formula: C13H18O4
• Molecular Weight: 238.284
• Mol file: 400737-27-1.mol

Synonyms:

Chemical Property of Butanal, 4-methoxy-3-[(4-methoxyphenyl)methoxy]-, (3R)-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Butanal, 4-methoxy-3-[(4-methoxyphenyl)methoxy]-, (3R)-

There total 2 articles about Butanal, 4-methoxy-3-[(4-methoxyphenyl)methoxy]-, (3R)- 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: 92.0%

2-[(R)-3-Methoxy-2-(4-methoxy-benzyloxy)-propyl]-[1,3]dithiane (400737-23-7) → (R)-4-Methoxy-3-(4-methoxy-benzyloxy)-butyraldehyde (400737-27-1)

Guidance literature:

With potassium carbonate; methyl iodide; In water; acetonitrile; at 45 ℃; for 5h;

DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

Reference yield:

(R)-1-[1,3]Dithian-2-yl-3-methoxy-propan-2-ol (400737-20-4) → (R)-4-Methoxy-3-(4-methoxy-benzyloxy)-butyraldehyde (400737-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 1 h / 25 °C

1.2: 99 percent / dimethylformamide / 4 h / 25 °C

2.1: 92 percent / aq. K₂CO₃ / acetonitrile / 5 h / 45 °C

With sodium hydride; potassium carbonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0304953

Reference yield: 98.0%

(Z)-(+)-crotyldiisopinocampheyl borane (99438-30-9) + (R)-4-Methoxy-3-(4-methoxy-benzyloxy)-butyraldehyde (400737-27-1) → (3R,4R,6R)-7-Methoxy-6-(4-methoxy-benzyloxy)-3-methyl-hept-1-en-4-ol (400737-30-6)

Guidance literature:

(Z)-(+)-crotyldiisopinocampheyl borane; (R)-4-Methoxy-3-(4-methoxy-benzyloxy)-butyraldehyde; With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃; for 2h;

With sodium perborate; In tetrahydrofuran; water; at 25 ℃; for 12h;

DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

upstream raw materials:

2-[(R)-3-Methoxy-2-(4-methoxy-benzyloxy)-propyl]-[1,3]dithiane

(R)-1-[1,3]Dithian-2-yl-3-methoxy-propan-2-ol

Downstream raw materials:

(3R,4R,6R)-7-Methoxy-6-(4-methoxy-benzyloxy)-3-methyl-hept-1-en-4-ol

(2S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-5-(4-methoxy-benzyloxy)-2-methyl-hexanal

tert-Butyl-{(1R,2R)-1-[(R)-3-methoxy-2-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyloxy}-dimethyl-silane

(R)-4-Benzyl-3-[(2R,3S,4R,5R,7R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-octanoyl]-oxazolidin-2-one

Refernces

• 1、 Nicolaou,Fylaktakidou, Konstantina C.,Monenschein, Holger,Li, Yiwei,Weyershausen, Bernd,Mitchell, Helen J.,Wei, Heng-Xu,Guntupalli, Prasuna,Hepworth, David,Sugita, Kazuyuki. "Total Synthesis of Apoptolidin: Construction of Enantiomerically Pure Fragments". . p. 15433 - 15442. Retrieved 2007/10/03.