(3AR,4R,6AS)-5-BENZYL-4-((S)-2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROLE

Base Information

• Chemical Name: (3AR,4R,6AS)-5-BENZYL-4-((S)-2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROLE
• CAS No.: 117770-02-2
• Molecular Formula: C19H27 N O4
• Molecular Weight: 333.428
• Mol file: 117770-02-2.mol

Synonyms:4H-1,3-Dioxolo[4,5-c]pyrrole,4-(2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydro-2,2-dimethyl-5-(phenylmethyl)-,[3aS-[3aa,4a(R*),6aa]]-

Chemical Property of (3AR,4R,6AS)-5-BENZYL-4-((S)-2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROLE

Chemical Property:

• PSA: 40.16000
• LogP: 2.48030

Purity/Quality:

97% ^*data from raw suppliers

(3AR,4R,6AS)-5-BENZYL-4-((S)-2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3AR,4R,6AS)-5-BENZYL-4-((S)-2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROLE

There total 4 articles about (3AR,4R,6AS)-5-BENZYL-4-((S)-2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROLE 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: 84.0%

(R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate (7115-24-4) + benzylamine (100-46-9) → (3aS,4S,6aR)-5-benzyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyrrole (117770-02-2)

Guidance literature:

In toluene; at 160 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1016/j.bmc.2019.03.056

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → (3aS,4S,6aR)-5-benzyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyrrole (117770-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium borohydride / ethanol / 0.5 h / Ambient temperature

2: 4,4-dimethylaminopyridine / pyridine / 2 h / 0 °C

3: 71 percent / 60 h / 60 - 70 °C

With sodium tetrahydroborate; dmap; In pyridine; ethanol;

DOI:10.1016/S0040-4020(01)81717-8

Reference yield:

2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol (3969-61-7) → (3aS,4S,6aR)-5-benzyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyrrole (117770-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 4,4-dimethylaminopyridine / pyridine / 2 h / 0 °C

2: 71 percent / 60 h / 60 - 70 °C

dmap; In pyridine;

DOI:10.1016/S0040-4020(01)81717-8

upstream raw materials:

(R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate

benzylamine

2,3,5,6-di-O-isopropylidene-D-mannofuranose

2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol

Downstream raw materials:

N-benzyl-1,4-dideoxy-1,4-imino-D-talitol

(S)-1-((3aS,4S,6aR)-5-benzyl-2,2-dimethyltetrahydro-4H-[1,3] dioxolo[4,5-c]pyrrol-4-yl)ethane-1,2-diol

N-benzyl-1,4-dideoxy-1,4-imino-D-talitol hydrochloride

C₁₉H₂₈BNO₆