D-Glucose diethyl dithioacetal

Base Information

• Chemical Name: D-Glucose diethyl dithioacetal
• CAS No.: 1941-52-2
• Molecular Formula: C10H22O5S2
• Molecular Weight: 286.414
• Hs Code.: 29400000
• European Community (EC) Number: 217-728-1
• DSSTox Substance ID: DTXSID101304066
• Nikkaji Number: J108.107A
• ChEMBL ID: CHEMBL1372335
• Mol file: 1941-52-2.mol

Synonyms:1941-52-2;D-Glucose diethyl dithioacetal;D-GLUCOSE DIETHYL MERCAPTAL;(2R,3R,4S,5R)-6,6-Bis(ethylthio)hexane-1,2,3,4,5-pentaol;D-glucosediethylmercaptal;(2R,3R,4S,5R)-6,6-bis(ethylsulfanyl)hexane-1,2,3,4,5-pentol;D-Glucose, diethyl dithioacetal;MLS000028527;D-Glucose diethylmercaptal;SMR000058293;D-Glucose-diethyldithioacetal;EINECS 217-728-1;AI3-20767;MFCD00004706;Opera_ID_1736;glucose diethyl dithioacetal;MLS001148077;SCHEMBL905563;CHEMBL1372335;C10H22O5S2;DTXSID101304066;HMS2234N22;AKOS004903192;C10-H22-O5-S2;CCG-249811;AS-70268;CS-0318351;G0259;D90738;A813702;(2R,3R,4S,5R)-6,6-Bis-Ethylsulfanyl-Hexane-1,2,3,4,5-Pentaol

Chemical Property of D-Glucose diethyl dithioacetal

Chemical Property:

• Appearance/Colour: white to light yellow crystal powde
• Vapor Pressure: 2.22E-15mmHg at 25°C
• Melting Point: 126-130 °C
• Refractive Index: -38.5 ° (C=2, H2O)
• Boiling Point: 570.3 °C at 760 mmHg
• PKA: 13.09±0.20(Predicted)
• Flash Point: 276.2 °C
• PSA: 151.75000
• Density: 1.357 g/cm³
• LogP: -0.74540
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 286.09086615
• Heavy Atom Count: 17
• Complexity: 190

Purity/Quality:

98%,99%, ^*data from raw suppliers

D-Glucose diethyl mercaptal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XnXi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-63-62-46-36/38-21
• Safety Statements: 24/25-53-36/37-26-25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCSC(C(C(C(C(CO)O)O)O)O)SCC
• Isomeric SMILES: CCSC([C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)SCC

Technology Process of D-Glucose diethyl dithioacetal

There total 7 articles about D-Glucose diethyl dithioacetal 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: 95.0%

2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal (4984-72-9) + ethyl α-(trifluoroacetoxy)acrylate (368-28-5) → D-glucose diethyl mercaptal (1941-52-2) + (R)-4-(Phenyl-hydrazono)-6-((1S,2R,3R)-1,2,3,4-tetrahydroxy-butyl)-dihydro-pyran-3-one

Guidance literature:

With methanol; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; for 3h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/0040-4020(95)01089-0

Reference yield: 91.6%

D-glucose (50-99-7) + ethanethiol (75-08-1) → D-glucose diethyl mercaptal (1941-52-2)

Guidance literature:

With dimethylbromosulphonium bromide; at 0 - 5 ℃; for 0.666667h; neat (no solvent);

DOI:10.1016/j.carres.2010.07.044

Reference yield: 88.0%

D-Glucose (2280-44-6) + ethanethiol (75-08-1) → D-glucose diethyl mercaptal (1941-52-2)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1039/c8cc05523h

upstream raw materials:

D-glucose

ethanethiol

glucose

O³,O⁵,O⁶-tribenzoyl-O¹,O²-isopropylidene-α-D-glucofuranose

Downstream raw materials:

penta-O-methyl-aldehydo-D-glucose diethyl dithioacetal

3,4,5,6-tetra-O-benzoyl-D-glucose diethyl dithioacetal

O²,O³,O⁴,O⁵-tetrabenzoyl-O⁶-trityl-D-glucose-diethyldithioacetal

(2R,3R,4S,5S,6R)-2-Ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Refernces

• 1、 Khan, Abu T.,Khan, Md. Musawwer. "Bromodimethylsulfonium bromide (BDMS) mediated dithioacetalization of carbohydrates under solvent-free conditions". . p. 2139 - 2145. Retrieved 2010.
• 2、 Barton,Jaszberenyi,Liu,Shinada. "The invention of radical reactions. Part XXXVI. Synthetic studies related to 3-deoxy-D-manno-2-octulosonic acid (KDO)". . p. 2717 - 2726. Retrieved 1996.
• 3、 Delbrouck, Julien A.,Bochatay, Valentin N.,Tikad, Abdellatif,Vincent, Stéphane P.. "Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification". supporting information. p. 5562 - 5566. Retrieved 2019/08/01.
• 4、 -. "Dapagliflozin impurity synthesis method". Paragraph 0004; 0018-0020. . Retrieved 2017/03/14.