[4S-(4α,5α(S^*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane

Base Information

• Chemical Name: [4S-(4α,5α(S^*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane
• CAS No.: 185699-87-0
• Molecular Formula: C₂₈H₄₀O₆Si
• Molecular Weight: 500.707

Synonyms:[4S-(4α,5α(S^*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane

Chemical Property of [4S-(4α,5α(S^*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane

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Technology Process of [4S-(4α,5α(S^*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane

There total 5 articles about [4S-(4α,5α(S^*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane 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: 99.0%

[4S-(4α,5α(S*))]-4-[(benzoyloxy)methyl]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-1,3-dioxolane (185699-86-9) → [4S-(4α,5α(S*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane (185699-87-0)

Guidance literature:

With sodium hydroxide; In methanol; for 23h; Ambient temperature;

DOI:10.1021/jo961372m

Reference yield:

2,3-O-isopropylidene-β-L-erythrofuranose (23262-84-2) → [4S-(4α,5α(S*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane (185699-87-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) MgCl₂, KI, K / 1.) THF, room temperature, 3 h, 2.) THF, room temperature, 18 h

2: 100 percent / Et₃N / CH₂Cl₂ / 7 h / -40 °C

3: 92 percent / 2,4,6-trimethylpyridine / CH₂Cl₂ / 19 h / Ambient temperature

4: 99 percent / NaOH / methanol / 23 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; sodium hydroxide; triethylamine; potassium iodide; magnesium chloride; In methanol; dichloromethane;

DOI:10.1021/jo961372m

Reference yield:

2-(2-bromophenyl)-2-phenyl-1,3-dioxolane (78105-68-7) → [4S-(4α,5α(S*))]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane (185699-87-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) MgCl₂, KI, K / 1.) THF, room temperature, 3 h, 2.) THF, room temperature, 18 h

2: 100 percent / Et₃N / CH₂Cl₂ / 7 h / -40 °C

3: 92 percent / 2,4,6-trimethylpyridine / CH₂Cl₂ / 19 h / Ambient temperature

4: 99 percent / NaOH / methanol / 23 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; sodium hydroxide; triethylamine; potassium iodide; magnesium chloride; In methanol; dichloromethane;

DOI:10.1021/jo961372m

upstream raw materials:

[4S-(4α,5α(S^*))]-4-[(benzoyloxy)methyl]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-1,3-dioxolane

2,3-O-isopropylidene-β-L-erythrofuranose

2-(2-bromophenyl)-2-phenyl-1,3-dioxolane

[4R-(4α[R^*],5α)]-2,2-dimethyl-α⁴-[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]-1,3-dioxolane-4,5-dimethanol

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