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

Base Information

• Chemical Name: 1-benzyloxy[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]methyl-(1R)-2-propenyl alcohol
• CAS No.: 344341-20-4
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 344341-20-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 1-benzyloxy[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]methyl-(1R)-2-propenyl alcohol 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:

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (19877-13-5) → 1-benzyloxy[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]methyl-(1R)-2-propenyl alcohol (344341-20-4)

Guidance literature:

Multi-step reaction with 3 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

With sodium tetrahydroborate; sulfuric acid; copper(II) sulfate; acetic acid; In ethanol;

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

Reference yield:

4-benzyloxy-5-vinyl-(3R,4S,5R)-tetrahydro-2,3-furandiol → 1-benzyloxy[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]methyl-(1R)-2-propenyl alcohol (344341-20-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / ethanol / 2 h / 20 °C

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

With sodium tetrahydroborate; sulfuric acid; copper(II) sulfate; In ethanol;

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

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

upstream raw materials:

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

Downstream raw materials:

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