(2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol

Base Information

• Chemical Name: (2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol
• CAS No.: 372987-10-5
• Molecular Formula: C₂₅H₃₄O₄
• Molecular Weight: 398.543

Synonyms:(2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol

Chemical Property of (2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol

Chemical Property:

Purity/Quality:

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Technology Process of (2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol

There total 9 articles about (2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol 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:

(4S,5R)-4,5-Bis-((S)-1-benzyloxymethyl-3-phenyl-propyl)-2,2-dimethyl-[1,3]dioxolane (372987-07-0) → (2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol (372987-10-5)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In water; ethyl acetate; at 20 ℃; for 63h;

DOI:10.1021/jm0011171

Reference yield:

phenylbutyric acid chloride (18496-54-3) → (2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol (372987-10-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 73 percent / NaH / dimethylformamide / 3 h / 0 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.5 h / 0 °C

2.2: DIEA / CH₂Cl₂ / 1 h / 0 °C

2.3: 74 percent / TiCl₄ / CH₂Cl₂ / 3 h

3.1: 89 percent / TMS-OTf / dioxane / 1 h

4.1: 83 percent / LAH / tetrahydrofuran / 1.5 h / -60 - 0 °C

5.1: 82 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -70 - 20 °C

6.1: 2.29 g / Zn; VCl₃(THF)3; DMI / CH₂Cl₂ / 20 h / 20 °C

7.1: 2.29 g / (+/-)-camphor-10-sulfonic acid / acetone / 0.5 h

8.1: 1.27 g / H₂; NaHCO₃ / Pd/C / ethyl acetate; H₂O / 63 h / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; desipramine; Vanadium (III) chloride-(tris-tetrahydrofuran); trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; titanium tetrachloride; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 5.1: Swern oxidation;

DOI:10.1021/jm0011171

Reference yield:

4-Phenylbutyric acid (1821-12-1) → (2S)-2-[(4R,5S)-5-[(1S)-1-(hydroxymethyl)-3-phenylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenyl-1-butanol (372987-10-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: SOCl₂; pyridine / 1.5 h / 20 - 40 °C

2.1: 73 percent / NaH / dimethylformamide / 3 h / 0 °C

3.1: TiCl₄ / CH₂Cl₂ / 0.5 h / 0 °C

3.2: DIEA / CH₂Cl₂ / 1 h / 0 °C

3.3: 74 percent / TiCl₄ / CH₂Cl₂ / 3 h

4.1: 89 percent / TMS-OTf / dioxane / 1 h

5.1: 83 percent / LAH / tetrahydrofuran / 1.5 h / -60 - 0 °C

6.1: 82 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -70 - 20 °C

7.1: 2.29 g / Zn; VCl₃(THF)3; DMI / CH₂Cl₂ / 20 h / 20 °C

8.1: 2.29 g / (+/-)-camphor-10-sulfonic acid / acetone / 0.5 h

9.1: 1.27 g / H₂; NaHCO₃ / Pd/C / ethyl acetate; H₂O / 63 h / 20 °C

With pyridine; lithium aluminium tetrahydride; thionyl chloride; oxalyl dichloride; desipramine; Vanadium (III) chloride-(tris-tetrahydrofuran); trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; titanium tetrachloride; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 6.1: Swern oxidation;

DOI:10.1021/jm0011171

upstream raw materials:

(4S,5R)-4,5-Bis-((S)-1-benzyloxymethyl-3-phenyl-propyl)-2,2-dimethyl-[1,3]dioxolane

phenylbutyric acid chloride

4-Phenylbutyric acid

(2S)-2-(benzyloxymethyl)-4-phenylbutanal

Downstream raw materials:

CH₃CN

(R)-2-{(4R,5S)-2,2-Dimethyl-5-[(R)-1-((S)-2-methyl-1-methylcarbamoyl-propylcarbamoyl)-3-phenyl-propyl]-[1,3]dioxolan-4-yl}-N-((S)-2-methyl-1-methylcarbamoyl-propyl)-4-phenyl-butyramide

succinimidyl (2R)-2-[(4R,5S)-5-(3-phenylpropyl-(1R)-1-succinimidyloxycarbonyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenylbutanoate

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