1,3-Dioxolane-4-ethanol, 2,2-dimethyl-, 3,5-dinitrobenzoate, (S)-

Base Information

• Chemical Name: 1,3-Dioxolane-4-ethanol, 2,2-dimethyl-, 3,5-dinitrobenzoate, (S)-
• CAS No.: 85287-65-6
• Molecular Formula: C₁₄H₁₆N₂O₈
• Molecular Weight: 340.29
• DSSTox Substance ID: DTXSID101167070
• Mol file: 85287-65-6.mol

Synonyms:DTXSID101167070;1,3-Dioxolane-4-ethanol, 2,2-dimethyl-, 3,5-dinitrobenzoate, (S)-;85287-65-6

Chemical Property of 1,3-Dioxolane-4-ethanol, 2,2-dimethyl-, 3,5-dinitrobenzoate, (S)-

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 340.09066547
• Heavy Atom Count: 24
• Complexity: 476

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OCC(O1)CCOC(=O)C2=CC(=CC(=C2)[N+](=O)[O-])[N+](=O)[O-])C
• Isomeric SMILES: CC1(OC[C@@H](O1)CCOC(=O)C2=CC(=CC(=C2)[N+](=O)[O-])[N+](=O)[O-])C

Technology Process of 1,3-Dioxolane-4-ethanol, 2,2-dimethyl-, 3,5-dinitrobenzoate, (S)-

There total 4 articles about 1,3-Dioxolane-4-ethanol, 2,2-dimethyl-, 3,5-dinitrobenzoate, (S)- 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: 41.0%

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (32233-43-5) + 3,5-dinitrobenoyl chloride (99-33-2) → 3,5-dinitrobenzoate of (3S)-3,4-(isopropylidenedioxy)butan-1-ol (85287-65-6)

Guidance literature:

With Me₂NC₅H₄N; triethylamine;

DOI:10.1016/S0040-4039(00)85738-X

Reference yield:

(S)-diethyl malate 2-(1-methyl-1-methoxyethyl ether) (66348-32-1) → 3,5-dinitrobenzoate of (3S)-3,4-(isopropylidenedioxy)butan-1-ol (85287-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1021/jo00376a011

Reference yield:

(E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol (106976-85-6) + 3,5-dinitrobenoyl chloride (99-33-2) → 3,5-dinitrobenzoate of benzyl alcohol (10478-07-6) + 3,5-dinitrobenzoate of (3S)-3,4-(isopropylidenedioxy)butan-1-ol (85287-65-6)

Guidance literature:

Multistep reaction;

DOI:10.1021/jo00386a034

upstream raw materials:

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

3,5-dinitrobenoyl chloride

(S)-1,2,4-butanetriol 2-(1-methyl-1-methoxyethyl ether)

(E)-(2S,3R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-pent-4-ene-2,3-diol

Downstream raw materials:

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

2-[(S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-phenoxycarbonyloxy-propyl]-oxazole-4-carboxylic acid methyl ester

2-[(R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-phenoxycarbonyloxy-propyl]-oxazole-4-carboxylic acid methyl ester