3-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

Base Information

• Chemical Name: 3-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose
• CAS No.: 2774-29-0
• Molecular Formula: C₁₂H₂₀O₅
• Molecular Weight: 244.288
• Hs Code.: 2940000080
• DSSTox Substance ID: DTXSID70541814
• Nikkaji Number: J987.710J
• Mol file: 2774-29-0.mol

Synonyms:3-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose;2774-29-0;(3aR,5S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole;3-Deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose;SCHEMBL12855280;DTXSID70541814;AKKRBVFGAWFTRW-LBTMZUADSA-N;AKOS030242217;3-Deoxy-1,2:5,6-di-O-isopropyliden-alpha-D-ribo Hexafuranose;3-Deoxy-1,2:5,6-di-O-isopropylidene- alpha -D-glucofuranose;(3aR, 5S, 6aR)-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 of 3-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 78-80 °C
• Refractive Index: 1.461
• Boiling Point: 291.049°C at 760 mmHg
• Flash Point: 111.989°C
• PSA: 46.15000
• Density: 1.124g/cm³
• LogP: 1.40440
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate
• 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:

99%, ^*data from raw suppliers

3-DEOXY-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE 95.00% ^*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
• Isomeric SMILES: CC1(OCC(O1)[C@@H]2C[C@@H]3[C@H](O2)OC(O3)(C)C)C
• Uses: An intermediate for 3-Deoxy-D-glucose

Technology Process of 3-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

There total 16 articles about 3-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-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: 98.0%

3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9) → (3aR,5R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (2774-29-0)

Guidance literature:

With hydrogen; nickel; In ethanol; for 6h; under 2068.59 Torr;

DOI:10.1016/j.tetlet.2006.03.116

Reference yield: 82.0%

3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9) → (3aR,5R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (2774-29-0)

Guidance literature:

With hydrogen; Rh/Al₂O₃; In ethyl acetate; under 735.5 Torr;

DOI:10.1016/S0040-4039(00)92630-3

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:

3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose

3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose

acetic acid methyl ester

ethyl acetate

Downstream raw materials:

3-Desoxy-D-galaktose

3-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose

1,3,6-trideoxy-1,6-imino-D-xylo-hexitol

(3aR,5R,6aR)-5-[(benzyloxy)methyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole