[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

Base Information

• Chemical Name: [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
• CAS No.: 185699-86-9
• Molecular Formula: C₃₅H₄₄O₇Si
• Molecular Weight: 604.816

Synonyms:[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

Chemical Property of [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

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Technology Process of [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

There total 4 articles about [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 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: 92.0%

t-butyldimethylsiyl triflate (69739-34-0) + [4S-(4α,5α(S*))]-4-[(benzoyloxy)methyl]-2,2-dimethyl-5-{[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]hydroxymethyl}-1,3-dioxolane (185699-85-8) → [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)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; for 19h; Ambient temperature;

DOI:10.1021/jo961372m

Reference yield:

2,3-O-isopropylidene-β-L-erythrofuranose (23262-84-2) → [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)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo961372m

Reference yield:

2-(2-bromophenyl)-2-phenyl-1,3-dioxolane (78105-68-7) → [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)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo961372m

upstream raw materials:

t-butyldimethylsiyl triflate

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

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

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

Downstream raw materials:

[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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