2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE

Base Information

• Chemical Name: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE
• CAS No.: 14152-97-7
• Molecular Formula: C15H19NO9S
• Molecular Weight: 389.383
• Hs Code.: 29329990
• European Community (EC) Number: 625-090-4
• DSSTox Substance ID: DTXSID90931112
• Nikkaji Number: J387.571G
• Mol file: 14152-97-7.mol

Synonyms:2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl isothiocyanate;GITC;NSC 224452;U 30213;

Chemical Property of 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE

Chemical Property:

• Vapor Pressure: 5.4E-09mmHg at 25°C
• Melting Point: 114-116 °C(lit.)
• Refractive Index: 1.556
• Boiling Point: 469.7 °C at 760 mmHg
• Flash Point: 237.8 °C
• PSA: 158.88000
• Density: 1.4 g/cm³
• LogP: 0.17230
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 389.07805236
• Heavy Atom Count: 26
• Complexity: 616

Purity/Quality:

98.0%min ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl isothiocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-42
• Safety Statements: 22-26-36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)N=C=S)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)N=C=S)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: Chiral reagent for resolution of amino acid derivatives.

Technology Process of 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE

There total 27 articles about 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE 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: 83.0%

2-methyl-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyrano)[2,1-d]-2-oxazoline (943860-86-4) + thiophosgene (463-71-8) → 2,3,4,6-tetra-O-Acetyl-β-D-galactopyranosyl isothiocyanate (14152-97-7,18866-59-6,93221-21-7,121959-10-2,121959-11-3,122564-52-7,41135-18-6)

Guidance literature:

With calcium carbonate; In dichloromethane; water; at 25 ℃; for 1h;

DOI:10.1021/jo062419z

Reference yield: 81.0%

trimethylsilyl isothiocyanate (2290-65-5) + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 2,3,4,6-tetra-O-Acetyl-β-D-galactopyranosyl isothiocyanate (14152-97-7,18866-59-6,93221-21-7,121959-10-2,121959-11-3,122564-52-7,41135-18-6)

Guidance literature:

With tin(IV) chloride; In dichloromethane; for 24h; Heating;

Reference yield: 70.0%

potassium thioacyanate (333-20-0) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 2,3,4,6-tetra-O-Acetyl-β-D-galactopyranosyl isothiocyanate (14152-97-7,18866-59-6,93221-21-7,121959-10-2,121959-11-3,122564-52-7,41135-18-6)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; In benzene; Heating;

upstream raw materials:

potassium thioacyanate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

lead(II) thiocyanate

trimethylsilyl isothiocyanate

Downstream raw materials:

N-[(1R,2R)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-thiourea

N-[(1S,2S)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-thiourea

N'-benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthiourea

1-methoxy(phenyl)thiophosphoryl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide

Refernces

• 1、 -. "Thiourea-containing arsenic sugar with anti-tumor activity and preparation method and application thereof". Paragraph 0024; 0026; 0030; 0037-0038; 0045; 0052-0053. . Retrieved 2020/04/02.
• 2、 Cuffaro, Doretta,Camodeca, Caterina,D'Andrea, Felicia,Piragine, Eugenia,Testai, Lara,Calderone, Vincenzo,Orlandini, Elisabetta,Nuti, Elisa,Rossello, Armando. "Matrix metalloproteinase-12 inhibitors: synthesis, structure-activity relationships and intestinal absorption of novel sugar-based biphenylsulfonamide carboxylates". . p. 5804 - 5815. Retrieved 2018/11/23.