Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate

Base Information

• Chemical Name: Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate
• CAS No.: 134639-13-7
• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.375
• Mol file: 134639-13-7.mol

Synonyms:Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate

Chemical Property of Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate

There total 1 articles about Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate 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:

benzyl bromide (100-39-0) + Methyl (2R,4S)-2-hydroxy-4,5-(isopropylidenedioxy)-2-methylpentanoate (134639-12-6) → Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate (134639-13-7)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1) DMF, -20 deg C, 2 h, 2) -20 deg C, 4 h;

DOI:10.1055/s-1991-26442

Reference yield: 75.0%

Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate (134639-13-7) → (2R,4S)-2-Benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanal (134639-14-8)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 3h;

DOI:10.1055/s-1991-26442

Reference yield:

Methyl (2R,4S)-2-benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanoate (134639-13-7) → (3S)-3-Benzyloxy-4-(1,4-dihydroxy-9,10-anthraquinon-2-yl)-3-methylbutanal (134639-16-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / DIBAL-H / toluene / 3 h / -78 °C

2: 1) piperidine, glac. AcOH, 2) O₂ / 1) i-PrOH, 25 deg C, 24 h, 2) 25 deg C, 30 min

3: 7.22 g / 90percent AcOH / 20 h / 25 °C

4: NaIO₄ / CH₂Cl₂; H₂O / 20 h / 25 °C

With piperidine; sodium periodate; oxygen; diisobutylaluminium hydride; acetic acid; In dichloromethane; water; toluene;

DOI:10.1055/s-1991-26442

upstream raw materials:

benzyl bromide

Methyl (2R,4S)-2-hydroxy-4,5-(isopropylidenedioxy)-2-methylpentanoate

Downstream raw materials:

(2R,4S)-2-Benzyloxy-4,5-(isopropylidenedioxy)-2-methylpentanal

(3S)-3-Benzyloxy-4-(1,4-dihydroxy-9,10-anthraquinon-2-yl)-3-methylbutanal

2-((S)-2-Benzyloxy-4,5-dihydroxy-2-methyl-pentyl)-1,4-dihydroxy-anthraquinone

2-<(2S)-2-Benzyloxy-1,4-dihydroxy-4,5-(isopropylidenedioxy)-pentyl>-2-methyl-9,10-anthraquinone