DIACETONE-D-GLUCOSE

Base Information

• Chemical Name: DIACETONE-D-GLUCOSE
• CAS No.: 14686-89-6
• Molecular Formula: C12H20O6
• Molecular Weight: 260.287
• Hs Code.: 29400090
• Mol file: 14686-89-6.mol

Synonyms:Gulofuranose,1,2:5,6-di-O-isopropylidene-, a-D- (8CI);Furo[2,3-d]-1,3-dioxole, a-D-gulofuranose deriv.;1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose;

Chemical Property of DIACETONE-D-GLUCOSE

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Vapor Pressure: 9.94E-07mmHg at 25°C
• Melting Point: 110-111 °C(lit.)
• Refractive Index: 1.483
• Boiling Point: 362.8 °C at 760 mmHg
• PKA: 13.15±0.60(Predicted)
• Flash Point: 173.2 °C
• PSA: 66.38000
• Density: 1.214 g/cm³
• LogP: 0.37520
• Storage Temp.: −20°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 260.12598835
• Heavy Atom Count: 18
• Complexity: 342

Purity/Quality:

98%, ^*data from raw suppliers

1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C
• Isomeric SMILES: CC1(OCC(O1)[C@H]2[C@H]([C@@H]3[C@H](O2)OC(O3)(C)C)O)C
• Uses: 1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose was a useful reagent in the preparation of fluorinated UDP-galactofuranose probes.

Technology Process of DIACETONE-D-GLUCOSE

There total 24 articles about DIACETONE-D-GLUCOSE 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%

3-O-acetyl-1,2,5,6-di-isopropylidene-α-D-glucofuranose (29586-98-9) → 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (582-52-5,2595-05-3,10368-86-2,13100-30-6,14686-89-6,23262-79-5,26597-74-0,26623-15-4,38166-58-4,38166-60-8,79943-22-9,83730-28-3) + acetic acid methyl ester (79-20-9)

Guidance literature:

With n-butylstannoic acid; In methanol; at 65.4 ℃; for 2h;

DOI:10.1016/S0040-4039(98)00241-X

Reference yield: 100.0%

Imidazole-1-sulfonic acid (3aR,6R,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 → (3aR,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (2595-05-3,14686-89-6,582-52-5,10368-86-2,13100-30-6,23262-79-5,26597-74-0,26623-15-4,38166-58-4,38166-60-8,79943-22-9,83730-28-3)

Guidance literature:

With sodium hydrogencarbonate; triethylamine; In methanol; for 8h; Irradiation;

DOI:10.1080/07328309808002900

Reference yield: 94.0%

Acetic acid (3aR,5S,6R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (16713-80-7,26775-14-4,29474-72-4,29586-98-9,38166-65-3,38166-66-4,38166-68-6,38166-69-7,98032-70-3,98975-57-6) → diacetone glucose (582-52-5,2595-05-3,10368-86-2,13100-30-6,14686-89-6,23262-79-5,26597-74-0,26623-15-4,38166-58-4,38166-60-8,79943-22-9,83730-28-3)

Guidance literature:

With sodium ethanolate; In ethanol; at 20 ℃;

DOI:10.1039/c39900000765

upstream raw materials:

L-glucose

acetone

1,2-O-isopropylidene-α-L-glucofuranose

(2S,3S,4S)-6-Nitro-hexane-1,2,3,4,5-pentaol

Downstream raw materials:

3-O-brosyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose

3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose

Benzoic acid (3aR,5R,6R,6aR)-5-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

[(3aR,5S,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]-carbamic acid benzyl ester

Refernces

• 1、 -. "GLUCOSIDE MONOMER, POLYMERIZATION COMPOSITION COMPRISING THE SAME AND HYDROGEL LENS USING THE SAME". Paragraph 0124-0130. . Retrieved 2019/08/22.
• 2、 Araújo, Noelia,Jenkinson, Sarah F.,Martínez, R. Fernando,Glawar, Andreas F. G.,Wormald, Mark R.,Butters, Terry D.,Nakagawa, Shinpei,Adachi, Isao,Kato, Atsushi,Yoshihara, Akihide,Akimitsu, Kazuya,Izumori, Ken,Fleet, George W. J.. "Synthesis from d-altrose of (5 R,6 R,7 R,8 S)-5,7-dihydroxy-8- hydroxymethylconidine and 2,4-dideoxy-2,4-imino-d-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-d-mannitol". supporting information; experimental part. p. 4174 - 4177. Retrieved 2012/10/23.