3-Chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose

Base Information

• Chemical Name: 3-Chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose
• CAS No.: 32785-94-7
• Molecular Formula: C12H19 Cl O5
• Molecular Weight: 278.73
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID10556765
• Nikkaji Number: J3.164.079B
• Wikidata: Q82438450
• Mol file: 32785-94-7.mol

Synonyms:32785-94-7;3-Chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose;(3aR,5R,6S,6aS)-6-chloro-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole;3-CHLORO-3-DEOXY-1,2;DTXSID10556765;(4R)-4-[(3aR,5R,6S,6aS)-6-chloro-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]-2,2-dimethyl-1,3-dioxolane

Chemical Property of 3-Chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose

Chemical Property:

• Boiling Point: 341.3±42.0 °C(Predicted)
• PSA: 46.15000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 1.62170
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 278.0921014
• Heavy Atom Count: 18
• Complexity: 345

Purity/Quality:

98%Min ^*data from raw suppliers

3-Chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-a-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)Cl)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@@H]2[C@@H]([C@@H]3[C@H](O2)OC(O3)(C)C)Cl)C

Technology Process of 3-Chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose

There total 8 articles about 3-Chloro-3-deoxy-1,2:5,6-di-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: 96.0%

Diacetone D-glucose (2595-05-3) → (3S)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose (32785-94-7)

Guidance literature:

Diacetone D-glucose; With sulfuryl dichloride; In dichloromethane; at -5 - 0 ℃; for 0.666667h; Inert atmosphere;

With 1,2,3-Benzotriazole; In dichloromethane; at 20 ℃; for 6.5h; Inert atmosphere;

DOI:10.1016/j.tet.2013.01.044

Reference yield: 85.0%

Trifluoro-methanesulfonic 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 (55951-90-1,74925-16-9,55951-93-4) → (3aR,6S,6aS)-6-Chloro-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (32785-94-7)

Guidance literature:

With tetrabutyl-ammonium chloride; In benzene; for 12h; Heating;

DOI:10.1021/jo01310a025

Reference yield: 57.0%

O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate (16667-96-2,28251-91-4,64481-59-0,64481-60-3,77454-06-9,77454-07-0,100638-80-0,100638-81-1,143037-49-4) → (3aR,5R,6S,6aS)-6-Chloro-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (32785-94-7,32785-97-0,74925-18-1)

Guidance literature:

With sulfuryl dichloride; In acetonitrile; 1.) 0 deg C, 1 h, 2.) 7 h, room temperature;

DOI:10.1016/0040-4039(88)85083-4

upstream raw materials:

3-chloro-3-deoxy-D-glucose

(1,2;5,6-Di-O-isopropyliden-α-D-allofuranos-3-yloxy)triphenylphosphonium-bromid

Diacetone D-glucose

O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate

Refernces

• 1、 Kozikowski, A. P.,Lee, Jaemoon. "A USEFUL METHOD FOR CONVERTING 2 ALCOHOLS TO THEIR CHLORIDES WITH RETENTION OF CONFIGURATION". . p. 3053 - 3056. Retrieved 2007/10/02.
• 2、 Binkley,Ambrose,Hehemann. "Synthesis of deoxyhalogeno sugars. Displacement of the (trifluoromethanesulfonyl)oxy (triflyl) group by halide ion". . p. 4387 - 4391. Retrieved 2007/10/02.