(6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Base Information

• Chemical Name: (6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
• CAS No.: 6893-72-7
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• NSC Number: 127670,102633,84317,21930
• DSSTox Substance ID: DTXSID30975636
• Mol file: 6893-72-7.mol

Synonyms:5-o-benzoyl-1,2-o-(1-methylethylidene)pentofuranose;6022-96-4;NSC102633;(6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate;6612-91-5;a-D-Ribofuranose, 1,2-O-(1-methylethylidene)-, 5-benzoate;NSC84317;NCIOpen2_007129;6893-72-7;SCHEMBL13871568;DTXSID30975636;WKRBIHIDJVMVGS-UHFFFAOYSA-N;((3aS,5R,6R,6aS)-6-Hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate;5460-57-1;NSC21930;NSC-21930;NSC-84317;NSC127670;AKOS023600040;NSC-102633;NSC-127670;Benzoic acid 6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

Chemical Property of (6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property:

• Vapor Pressure: 3.14E-08mmHg at 25°C
• Refractive Index: 1.532
• Boiling Point: 432°C at 760 mmHg
• Flash Point: 159.2°C
• Density: 1.253g/cm³
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 294.11033829
• Heavy Atom Count: 21
• Complexity: 390

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)COC(=O)C3=CC=CC=C3)O)C

Technology Process of (6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

There total 5 articles about (6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 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: 42.0%

5-O-benzoyl-L-arabinose diethyl dithioacetal (77772-43-1) + acetone (67-64-1) → 5-O-benzoyl-1,2-O-isopropylidene-β-L-arabinofuranose (6893-72-7)

Guidance literature:

With mercury dichloride;

DOI:10.1016/0008-6215(92)84166-P

Reference yield: 37.0%

methyl 5-O-benzoyl-β-L-arabinoside (1333476-18-8) + acetone (67-64-1) → 5-O-benzoyl-1,2-O-isopropylidene-β-L-arabinofuranose (6893-72-7)

Guidance literature:

With sulfuric acid; copper(II) sulfate; at 20 ℃; for 24h;

DOI:10.1135/cccc2011038

Reference yield:

benzoyl chloride (98-88-4) → 5-O-benzoyl-1,2-O-isopropylidene-β-L-arabinofuranose (6893-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 18 h / -78 °C

2: sulfuric acid; copper(II) sulfate / 24 h / 20 °C

With sulfuric acid; copper(II) sulfate; triethylamine; In dichloromethane;

DOI:10.1135/cccc2011038

upstream raw materials:

5-O-benzoyl-L-arabinose diethyl dithioacetal

acetone

L-arabinose di(ethylthio)acetal

methyl 5-O-benzoyl-β-L-arabinoside

Downstream raw materials:

3,5-di-O-benzoyl-1,2-O-isopropylidene-β-L-arabinofuranose

methyl 3,5-di-O-benzoyl-L-arabinofuranoside

1,2-Di-O-acetyl-3,5-di-O-benzoyl-L-arabinofuranose

methyl 3,5-di-O-benzoyl-2-deoxy-L-erythro-pentofuranoside