(2S,4S)-2-Benzyloxy-4,5-isopropylidenedioxypentanal

Base Information

• Chemical Name: (2S,4S)-2-Benzyloxy-4,5-isopropylidenedioxypentanal
• CAS No.: 135283-68-0
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 135283-68-0.mol

Synonyms:

Chemical Property of (2S,4S)-2-Benzyloxy-4,5-isopropylidenedioxypentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-2-Benzyloxy-4,5-isopropylidenedioxypentanal

There total 3 articles about (2S,4S)-2-Benzyloxy-4,5-isopropylidenedioxypentanal 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) → (2S,4S)-2-Benzyloxy-4,5-isopropylidenedioxypentanal (135283-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: silver(l) oxide; potassium iodide / dichloromethane / 4 h / 25 °C

2.1: diisobutylaluminium hydride / toluene; dichloromethane / 1 h / -78 °C

2.2: 28 °C / Inert atmosphere

With diisobutylaluminium hydride; potassium iodide; silver(l) oxide; In dichloromethane; toluene;

DOI:10.1021/acs.orglett.8b00901

Reference yield:

(2S,4S)-4-O-Benzyl-1,2-O-isopropylidene-5-hexene-1,2,4-triol (135256-33-6) → (2S,4S)-2-Benzyloxy-4,5-isopropylidenedioxypentanal (135283-68-0)

Guidance literature:

With dimethylsulfide; ozone; Yield given. Multistep reaction; 1) MeOH, -78 deg C, 2) up to 22 deg C;

Reference yield:

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (32233-43-5) → (2S,4S)-2-Benzyloxy-4,5-isopropylidenedioxypentanal (135283-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) oxalyl chloride, DMSO, 2) ethyldiisopropylamine / 1) CH₂Cl₂, -60 deg C, 10 min, 2) 2 h

3: 1) O₃, 2) dimethyl sulfide / 1) MeOH, -78 deg C, 2) up to 22 deg C

With oxalyl dichloride; dimethylsulfide; ozone; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;

upstream raw materials:

(2S,4S)-4-O-Benzyl-1,2-O-isopropylidene-5-hexene-1,2,4-triol

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

benzyl bromide

Downstream raw materials:

(2S,4S,5S)-4-O-Benzyl-1,2-O-isopropylidene-5-phthalimido-6-heptene-1,2,4-triol

(2S,4S,5R)-4-O-Benzyl-1,2-O-isopropylidene-5-phthalimido-6-heptene-1,2,4-triol

(2S,4S,5R)-5-Acetamido-4-O-benzyl-1,2-O-isopropylidene-6-heptene-1,2,4-triol

(2S,4S,5S)-5-Acetamido-4-O-benzyl-1,2-O-isopropylidene-6-heptene-1,2,4-triol