1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose S-Methyl Dithiocarbonate

Base Information

• Chemical Name: 1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose S-Methyl Dithiocarbonate
• CAS No.: 16667-96-2
• Molecular Formula: C14H22 O6 S2
• Molecular Weight: 350.457
• Mol file: 16667-96-2.mol

Synonyms:Glucofuranose,1,2:5,6-di-O-isopropylidene-, S-methyl dithiocarbonate, a-D- (6CI,7CI,8CI);a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, S-methyl carbonodithioate (9CI);Carbonicacid, dithio-, S-methyl ester, O-ester with 1,2:5,6-di-O-isopropylidene-a-D-glucofuranose (8CI);1,2:5,6-Di-O-Isopropylidene-3-O-(methylthio)thiocarbonyl-a-D-glucofuranose;NSC 409733;

Chemical Property of 1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose S-Methyl Dithiocarbonate

Chemical Property:

• Vapor Pressure: 4.16E-07mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 427.2°Cat760mmHg
• Flash Point: 212.2°C
• PSA: 112.77000
• Density: 1.33g/cm³
• LogP: 2.04740
• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

98% ^*data from raw suppliers

1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose S-methyl dithiocarbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose S-Methyl Dithiocarbonate (cas# 16667-96-2) is a compound useful in organic synthesis.

Technology Process of 1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose S-Methyl Dithiocarbonate

There total 16 articles about 1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose S-Methyl Dithiocarbonate 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%

carbon disulfide (75-15-0,12122-00-8) + 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-α-D-glucofuranose-3-O-(S-methylxanthate) (16667-96-2)

Guidance literature:

carbon disulfide; 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With 1H-imidazole; sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1021/jo991715r

Reference yield: 100.0%

C13H20O6S2 + methyl iodide (74-88-4) → 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)

Guidance literature:

for 1.5h;

DOI:10.1016/j.carres.2013.10.012

Reference yield: 94.0%

carbon disulfide (75-15-0,12122-00-8) + methyl bromide (74-83-9) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) → 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)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In benzene; for 0.75h;

upstream raw materials:

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

carbon disulfide

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

methyl iodide

Downstream raw materials:

1,2:5,6-Di-O-isopropyliden-3-S-(methylthio)-carbonyl-3-thio-α-D-glucofuranose

3β-<((trifluoromethyl)phenylmethyl)imino>-3-deoxy-1,2:5,6-di-O-isopropylidene-D-glucofuranose

3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

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