[(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(phenylmethanone)

Base Information

• Chemical Name: [(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(phenylmethanone)
• CAS No.: 167282-09-9
• Molecular Formula: C19H18O4
• Molecular Weight: 310.35
• DSSTox Substance ID: DTXSID90576163
• Nikkaji Number: J1.553.789B
• Wikidata: Q82465717

Synonyms:167282-09-9;[(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(phenylmethanone);DTXSID90576163

Chemical Property of [(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(phenylmethanone)

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 310.12050905
• Heavy Atom Count: 23
• Complexity: 404

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(C(O1)C(=O)C2=CC=CC=C2)C(=O)C3=CC=CC=C3)C
• Isomeric SMILES: CC1(O[C@H]([C@@H](O1)C(=O)C2=CC=CC=C2)C(=O)C3=CC=CC=C3)C

Technology Process of [(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(phenylmethanone)

There total 7 articles about [(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(phenylmethanone) 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: 96.0%

phenylmagnesium chloride (100-59-4) + (4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide (177283-77-1) → (-)-((4R,5R)-5-benzoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methanone (167282-09-9)

Guidance literature:

In tetrahydrofuran; at 22 ℃; for 2.25h;

DOI:10.1016/S0040-4039(01)01085-1

Reference yield: 95.0%

(4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide (177283-77-1) → (-)-((4R,5R)-5-benzoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methanone (167282-09-9)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/jo062016z

Reference yield: 86.0%

phenylmagnesium bromide + (4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide (177283-77-1) → (-)-((4R,5R)-5-benzoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methanone (167282-09-9)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.tetasy.2005.05.002

upstream raw materials:

(4R,5R)-2,2,N,N,N',N'-hexamethyl-1,3-dioxolane-4,5-dicarboxamide

phenylmagnesium chloride

(4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide

(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxyl dichloride

Downstream raw materials:

(αS,α'S,4R,5R)-2,2,α,α'-tetramethyl-α,α'-diphenyl-1,3-dioxolane-4,5-dimethanol

(4S,5S)-4,5-bis[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane

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

(αR,α'R,4R,5R)-α,α'-diethyl-2,2-dimethyl-α,α'-diphenyl-1,3-dioxolane-4,5-dimethanol

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