3-O-Acetyl-1,2-O-isopropylidene-a-D-glucofuranose

Base Information

• Chemical Name: 3-O-Acetyl-1,2-O-isopropylidene-a-D-glucofuranose
• CAS No.: 24807-96-3
• Molecular Formula: C11H18O7
• Molecular Weight: 262.26
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID60451397
• Nikkaji Number: J1.180.957J
• Wikidata: Q82271403
• Mol file: 24807-96-3.mol

Synonyms:24807-96-3;3-O-Acetyl-1,2-O-isopropylidene-a-D-glucofuranose;3-O-ACETYL-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE;[(3aR,5R,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate;1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE3-ACETATE;DTXSID60451397;W-202038;1-O,2-O-Isopropylidene-alpha-D-glucofuranose 3-acetate;a-D-Glucofuranose,1,2-O-(1-methylethylidene)-,3-acetate;3-O-Acetyl-1,2-O-(1-methylethylidene)-alpha-D-xylo-hexofuranose;(3AR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl acetate;(3AR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ylacetate

Chemical Property of 3-O-Acetyl-1,2-O-isopropylidene-a-D-glucofuranose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 391.98 °C at 760 mmHg
• Flash Point: 148.45 °C
• PSA: 94.45000
• Density: 1.356 g/cm³
• LogP: -0.85230
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 262.10525291
• Heavy Atom Count: 18
• Complexity: 329

Purity/Quality:

99% ^*data from raw suppliers

(3AR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ylacetate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C2C(OC1C(CO)O)OC(O2)(C)C
• Isomeric SMILES: CC(=O)O[C@@H]1[C@@H]2[C@H](O[C@@H]1[C@@H](CO)O)OC(O2)(C)C

Technology Process of 3-O-Acetyl-1,2-O-isopropylidene-a-D-glucofuranose

There total 6 articles about 3-O-Acetyl-1,2-O-isopropylidene-a-D-glucofuranose 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: 94.0%

Acetic acid (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (98032-70-3) → 3-O-acetyl-1,2-O-isopropylidene-β-L-idofuranose (24807-96-3,51433-05-7,109680-96-8,130995-73-2,141946-78-3)

Guidance literature:

With lanthanum(III) nitrate; In acetonitrile; for 5h; Heating;

DOI:10.1016/j.tetlet.2005.08.081

Reference yield: 90.0%

methanol (67-56-1) + Acetic acid (3aR,5R,6S,6aR)-5-{(R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-1-hydroxy-ethyl}-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester → 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (24807-96-3) + bis(4-methoxyphenyl)phenylmethyl methyl ether (125016-87-7)

Guidance literature:

With lithium tetrafluoroborate; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1080/00397919908085970

Reference yield:

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (16713-80-7) → 2,2-dimethyl-4-phenyl-1,3-dioxolane (52129-03-0) + 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (24807-96-3)

Guidance literature:

With phenylethane 1,2-diol; toluene-4-sulfonic acid; In dichloromethane; for 0.5h;

DOI:10.1016/S0008-6215(00)90486-5

upstream raw materials:

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose

methanol

3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexo-5-enofuranose

Acetic acid (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Downstream raw materials:

O³-acetyl-O¹,O²-isopropylidene-O⁶-trityl-α-D-glucofuranose

O³-acetyl-O⁵,O⁶-dibenzoyl-O¹,O²-isopropylidene-α-D-glucofuranose

3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose

3-O-acetyl-1,2-O-isopropylidene-6-O-tosyl-D-glucofuranose