(4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Base Information

• Chemical Name: (4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
• CAS No.: 86348-30-3
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.392
• Mol file: 86348-30-3.mol

Synonyms:(4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Chemical Property of (4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

There total 9 articles about (4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 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: 91.0%

Acetic acid ((4S,5S)-5-benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenylsulfanyl-methyl ester (1048386-96-4) → (4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (86348-30-3)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)97596-9

Reference yield:

(E)-4-(benzhydryloxy)but-2-enal (128990-34-1) → (4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (86348-30-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / NaBH₄ / methanol / 3 h / -20 - -10 °C

2: 92 percent / t-BuOCl, L-(+)-diisopropyl tartrate*Ti(OiPr)4 / CH₂Cl₂ / -20 °C

3: 71 percent / 0.5N NaOH / 2-methyl-propan-2-ol / Heating

4: POCl₃ / CH₂Cl₂ / Ambient temperature

5: m-chloroperoxybenzoic acid / CH₂Cl₂ / -78 °C

6: NaOAc / 8 h / Heating

7: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

With sodium hydroxide; sodium tetrahydroborate; tert-butylhypochlorite; L-(+)-diisopropyl tartrate*Ti(OiPr)4; sodium acetate; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In methanol; hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)97596-9

Reference yield:

(2S,3S)-4-Benzhydryloxy-2,3-epoxy-1-butanol (86348-28-9,99745-06-9) → (4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (86348-30-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / 0.5N NaOH / 2-methyl-propan-2-ol / Heating

2: POCl₃ / CH₂Cl₂ / Ambient temperature

3: m-chloroperoxybenzoic acid / CH₂Cl₂ / -78 °C

4: NaOAc / 8 h / Heating

5: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

With sodium hydroxide; sodium acetate; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)97596-9

upstream raw materials:

Acetic acid ((4S,5S)-5-benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenylsulfanyl-methyl ester

(E)-4-(benzhydryloxy)but-2-enal

(2S,3S)-4-Benzhydryloxy-2,3-epoxy-1-butanol

(4S,5S)-4-Benzhydryloxymethyl-2,2-dimethyl-5-phenylsulfanylmethyl-[1,3]dioxolane

Downstream raw materials:

(E)-3-((4R,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propenal

[(2R,3R)-3-((4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-methanol

[(2S,3S)-3-((4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-methanol

(E)-3-((4R,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol