5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

Base Information

• Chemical Name: 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS No.: 4613-62-1
• Molecular Formula: C12H20 O5
• Molecular Weight: 244.288
• NSC Number: 59397
• Nikkaji Number: J517.551H
• Mol file: 4613-62-1.mol

Synonyms:4613-62-1;5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole;alpha-D-xylo-Hexofuranose, 3-deoxy-1,2:5,6-bis-O-(1-methylethylidene)-;3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane;2774-29-0;NSC59397;SCHEMBL8126222;NSC-59397;FT-0665790;A-D-RIBO-HEXOFURANOSE,3-DEOXY-1,2:5,6-BIS-O-(1-METHYLETHYLIDENE)-

Chemical Property of 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

• Vapor Pressure: 0.00348mmHg at 25°C
• Boiling Point: 291°Cat760mmHg
• Flash Point: 112°C
• PSA: 46.15000
• Density: 1.123g/cm³
• LogP: 1.40440
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 244.13107373
• Heavy Atom Count: 17
• Complexity: 314

Purity/Quality:

97% ^*data from raw suppliers

3-Deoxy-1,2:5,6-di-O-isopropylidene-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)C2CC3C(O2)OC(O3)(C)C)C
• Uses: An intermediate for 3-Deoxy-D-glucose.

Technology Process of 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

There total 12 articles about 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 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%

triethylsilane (617-86-7) + 1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose (130534-83-7) → 4-Fluorophenol (371-41-5) + triethylsilyl benzoate (1018-20-8) + triethyl(para-fluorophenoxy)silane + 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside (4613-62-1)

Guidance literature:

With dibenzoyl peroxide; In toluene; Product distribution; Mechanism; Heating; other reagents, other substrates;

DOI:10.1016/S0040-4020(01)80380-X

Reference yield: 91.0%

1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) (16667-96-2) → 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside (4613-62-1) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); hypophosphorous acid; triethylamine; In 1,4-dioxane; for 0.75h; Heating; other substrates, other base, other times, also with dimethyl phosphite;

DOI:10.1016/0040-4039(92)89012-2

Reference yield: 69.0%

1,2:5,6-di-O-isopropylidene-3-O-(pentafluorophenoxy)thionocarbonylglucofuranose → 3-Desoxy-1,2:5,6-di-O-isopropyliden-D-ribo-hexofuranose (2774-29-0,4613-62-1,22248-86-8,32785-98-1,81097-00-9)

Guidance literature:

With sodium hypophosphite; tetra(n-butyl)ammonium hydroxide; 4,4'-dicyano-4,4'-azo-di-valeric acid; In 2-methoxy-ethanol; at 45 ℃; for 0.166667h; pH=8.0;

DOI:10.1021/jo991645o

upstream raw materials:

triethylsilane

1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose

3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Diethyl-thiocarbamic acid O-[(3aR,5R,6S,6aR)-5-((R)-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:

3-deoxy-1,2-O-isopropylidene-D-glucose

3-Desoxy-D-galaktose

(2R,4R)-6-Benzyloxy-hexane-1,2,4-triol

3-deoxy-1,2:5,6-tetra-O-acetyl-β-D-glucofuranose

Refernces

• 1、 Bowman, W. Russell,Krintel, Sussie L.,Schilling, Mark B.. "Tributylgermanium hydride as a replacement for tributyltin hydride in radical reactions". . p. 585 - 592. Retrieved 2007/10/03.
• 2、 Barton,Jang,Jaszberenyi Cs.. "The invention of radical reactions. Part XXIX. Radical mono- and dideoxygenations with silanes". . p. 2793 - 2804. Retrieved 2007/10/02.