(2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal

Base Information

• Chemical Name: (2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal
• CAS No.: 912653-92-0
• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.392
• Mol file: 912653-92-0.mol

Synonyms:(2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal

Chemical Property of (2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal

There total 6 articles about (2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal 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: 75.0%

1-(((3R,4S,5S)-5-methoxy-3,7-dimethyloct-1-on-4-yloxy)methyl)benzene (912653-91-9) → (2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal (912653-92-0)

Guidance literature:

1-(((3R,4S,5S)-5-methoxy-3,7-dimethyloct-1-on-4-yloxy)methyl)benzene; With ozone; In methanol; dichloromethane; at -78 ℃;

With triphenylphosphine; In methanol; dichloromethane; at -78 - 20 ℃; for 0.75h;

DOI:10.1016/j.bmc.2006.05.056

Reference yield:

(S)-2-hydroxyl-3,3-dimethylbutyric acid (13748-90-8,498-36-2) → (2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal (912653-92-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 100 percent / trimethylsilyl chloride; 2,2-dimethoxypropane / 16 h / 20 °C

2.1: 73 percent / sodium hydride / dimethylformamide / 5 h / 20 °C

3.1: 97 percent / LiAlH₄ / diethyl ether / 3 h / 20 °C

4.1: 79 percent / tetramethylpiperidine-N-oxyl; potassium bromide; NaHCO₃ / NaClO / H₂O; CH₂Cl₂ / 0 °C

5.1: BF₃*Et₂O / CH₂Cl₂ / 12 h / -78 °C

5.2: 60 percent / sodium hydride; Bu₄NI / dimethylformamide / 1.5 h / 20 °C

6.1: ozone / CH₂Cl₂; methanol / -78 °C

6.2: 75 percent / triphenylphosphine / CH₂Cl₂; methanol / 0.75 h / -78 - 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium aluminium tetrahydride; chloro-trimethyl-silane; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; ozone; 2,2-dimethoxy-propane; potassium bromide; sodium hypochlorite; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.05.056

Reference yield:

methyl (2S)-2-hydroxy-4-methylpentanoate (17392-84-6) → (2S,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptanal (912653-92-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 73 percent / sodium hydride / dimethylformamide / 5 h / 20 °C

2.1: 97 percent / LiAlH₄ / diethyl ether / 3 h / 20 °C

3.1: 79 percent / tetramethylpiperidine-N-oxyl; potassium bromide; NaHCO₃ / NaClO / H₂O; CH₂Cl₂ / 0 °C

4.1: BF₃*Et₂O / CH₂Cl₂ / 12 h / -78 °C

4.2: 60 percent / sodium hydride; Bu₄NI / dimethylformamide / 1.5 h / 20 °C

5.1: ozone / CH₂Cl₂; methanol / -78 °C

5.2: 75 percent / triphenylphosphine / CH₂Cl₂; methanol / 0.75 h / -78 - 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; ozone; potassium bromide; sodium hypochlorite; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.05.056

upstream raw materials:

1-(((3R,4S,5S)-5-methoxy-3,7-dimethyloct-1-on-4-yloxy)methyl)benzene

(S)-2-methoxy-4-methylpentanal

(S)-2-hydroxyl-3,3-dimethylbutyric acid

methyl (2S)-2-hydroxy-4-methylpentanoate

Downstream raw materials:

(2R,3S,4S)-3-benzyloxy-4-methoxy-2,6-dimethylheptan-1-ol