O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate

Base Information

• Chemical Name: O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate
• CAS No.: 888725-60-8
• Molecular Formula: C₂₁H₂₈F₃NO₆S
• Molecular Weight: 479.518
• Mol file: 888725-60-8.mol

Synonyms:O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate

Chemical Property of O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate

There total 6 articles about O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate 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: 95.0%

tert-butyl (1R,2R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3,3-trifluoro-2-(hydroxymethyl)propylcarbonate (888725-59-5) + phenylcarbonochloridothioate (1005-56-7) → O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate (888725-60-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1021/jo0601157

Reference yield:

(R)-2-((R)-(benzylamino)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropan-1-ol (888725-58-4) → O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate (888725-60-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C / ethyl acetate / 4 h / 20 °C

2: 95 percent / pyridine; DMAP / CH₂Cl₂ / 6 h / 20 °C

With pyridine; dmap; hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jo0601157

Reference yield:

N-benzyl-N-((1R,2S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trifluoromethyl)but-3-enyl)-2,2,2-trifluoroacetamide (888725-57-3) → O-benzyl O-(R)-2-((R)-(tert-butoxycarbonyl)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropyl carbothionate (888725-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 86 percent / NaBH₄ / CH₂Cl₂; ethanol / 3 h / 20 °C

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 4 h / 20 °C

3.1: 95 percent / pyridine; DMAP / CH₂Cl₂ / 6 h / 20 °C

With pyridine; dmap; hydrogen; ozone; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jo0601157

upstream raw materials:

tert-butyl (1R,2R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3,3-trifluoro-2-(hydroxymethyl)propylcarbonate

phenylcarbonochloridothioate

(1R,2S)-N-benzyl-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trifluoromethyl)but-3-en-1-amine

(R)-2-((R)-(benzylamino)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,3,3-trifluoropropan-1-ol

Downstream raw materials:

(2R,3S)-2-(tert-butoxycarbonyl)-4,4,4-trifluoro-3-methylbutanoic acid