3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene

Base Information

• Chemical Name: 3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene
• CAS No.: 344341-21-5
• Molecular Formula: C₂₃H₂₈O₄
• Molecular Weight: 368.473
• Mol file: 344341-21-5.mol

Synonyms:3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene

Chemical Property of 3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene

There total 4 articles about 3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene 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: 85.0%

benzyl bromide (100-39-0) + 1-benzyloxy[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]methyl-(1R)-2-propenyl alcohol (344341-20-4) → 3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene (344341-21-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(01)00098-2

Reference yield:

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (19877-13-5) → 3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene (344341-21-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / aq. AcOH; conc. H₂SO₄ / 48 h / 20 °C

2: NaBH₄ / ethanol / 2 h / 20 °C

3: 1.21 g / CuSO₄; conc. H₂SO₄ / 12 h / 20 °C

4: 85 percent / NaH / dimethylformamide

With sodium tetrahydroborate; sulfuric acid; sodium hydride; copper(II) sulfate; acetic acid; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(01)00098-2

Reference yield:

4-benzyloxy-5-vinyl-(3R,4S,5R)-tetrahydro-2,3-furandiol → 3,4-dibenzyloxy-4-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(3R)-1-butene (344341-21-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / ethanol / 2 h / 20 °C

2: 1.21 g / CuSO₄; conc. H₂SO₄ / 12 h / 20 °C

3: 85 percent / NaH / dimethylformamide

With sodium tetrahydroborate; sulfuric acid; sodium hydride; copper(II) sulfate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(01)00098-2

upstream raw materials:

benzyl bromide

1-benzyloxy[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]methyl-(1R)-2-propenyl alcohol

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

(2S,3S,4R)-3-benzyloxy-5-hexen-1,2,4-triol