(3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-4-methoxy-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Base Information

• Chemical Name: (3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-4-methoxy-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane
• CAS No.: 43138-64-3
• Molecular Formula: C13H22 O6
• Molecular Weight: 274.314
• DSSTox Substance ID: DTXSID901176160
• Nikkaji Number: J75.590G
• Mol file: 43138-64-3.mol

Synonyms:43138-64-3;(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole;(3R,4S)-3-[(4R)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YL]-4-METHOXY-7,7-DIMETHYL-2,6,8-TRIOXABICYCLO[3.3.0]OCTANE;SCHEMBL6909282;.alpha.-D-Glucofuranose, 3-O-methyl-1,2:5,6-bis-O-(1-methylethylidene)-;DTXSID901176160;1-O,2-O:5-O,6-O-Diisopropylidene-3-O-methyl-alpha-D-glucofuranose;|A-D-Glucofuranose, 3-O-methyl-1,2:5,6-bis-O-(1-methylethylidene)-;3-O-Methyl-1,2:5,6-bis-O-(1-methylethylidene)-alpha-D-glucofuranose;(4R)-4-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]-2,2-dimethyl-1,3-dioxolane

Chemical Property of (3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-4-methoxy-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Chemical Property:

• Vapor Pressure: 0.00064mmHg at 25°C
• Boiling Point: 319.3°Cat760mmHg
• Flash Point: 124.2°C
• PSA: 55.38000
• Density: 1.2g/cm³
• LogP: 1.02930
• Solubility.: Ethyl Acetate
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 274.14163842
• Heavy Atom Count: 19
• Complexity: 355

Purity/Quality:

97% ^*data from raw suppliers

1,2:5,6-Diisopropylidene-3-O-methyl-α-D-glucofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)OC)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@@H]2[C@@H]([C@@H]3[C@H](O2)OC(O3)(C)C)OC)C
• Uses: Glucofuranose derivative with antiinflammatory, antipyretic, analgesic, and antispasmodic activities.

Technology Process of (3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-4-methoxy-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

There total 22 articles about (3R,4S)-3-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-YL]-4-methoxy-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane 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: 100.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) + methyl iodide (74-88-4) → 1,2-:5,6-di-O-isopropylidene-3-O-methyl-α-D-glucofuranose (43138-64-3)

Guidance literature:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 1h;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1021/jacs.8b11882

Reference yield: 95.0%

dimethyl sulfate (77-78-1) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2-:5,6-di-O-isopropylidene-3-O-methyl-α-D-glucofuranose (43138-64-3)

Guidance literature:

With sodium hydroxide; tetrabutyl-ammonium chloride; In benzene; at 20 ℃; for 0.2h;

Reference yield: 86.0%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2-:5,6-di-O-isopropylidene-3-O-methyl-α-D-glucofuranose (43138-64-3)

Guidance literature:

Hakomori's methylation;

upstream raw materials:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose potassium salt

Natrium-Verbindung der O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

3-O-methyl-D-glucose

Downstream raw materials:

3-O-methyl-D-glucose

C₂₆H₃₅O₅SiN₃

6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-α-D-allofuranose

6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose

Refernces

• 1、 Foss, Per,Skulberg, Olav M.,Kilaas, Lars,Liaaen-Jensen, Synnoeve. "THE CARBOHYDRATE MOIETIES BOUND TO THE CAROTENOIDS MYXOL AND OSCILLOL AND THEIR CHEMOSYSTEMATIC APPLICATIONS". . p. 1127 - 1132. Retrieved 1986.
• 2、 Yu, Yang,Gim, Soeun,Kim, Dongyoon,Arnon, Zohar A.,Gazit, Ehud,Seeberger, Peter H.,Delbianco, Martina. "Oligosaccharides Self-Assemble and Show Intrinsic Optical Properties". supporting information. p. 4833 - 4838. Retrieved 2019/03/26.
• 3、 -. "Furan glucosyl triazole type compound and preparation method and bactericide thereof". Paragraph 0050-0053. . Retrieved 2018/04/21.