4-Isothiocyanatophenyl alpha-D-mannopyranoside

Base Information

• Chemical Name: 4-Isothiocyanatophenyl alpha-D-mannopyranoside
• CAS No.: 96345-79-8
• Molecular Formula: C13H15 N O6 S
• Molecular Weight: 313.331
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID50452318
• Nikkaji Number: J852.967A
• Mol file: 96345-79-8.mol

Synonyms:96345-79-8;4-Isothiocyanatophenyl alpha-D-mannopyranoside;4-Isothiocyanatophenyl-a-D-mannopyranoside;alpha-D-Mannopyranosylphenyl isothiocyanate;a-D-Mannopyranoside, 4-isothiocyanatophenyl;4-Isothiocyanatophenyl |A-D-Mannopyranoside;(2R,3S,4S,5S,6R)-2-(HYDROXYMETHYL)-6-(4-ISOTHIOCYANATOPHENOXY)OXANE-3,4,5-TRIOL;(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol;SCHEMBL6683484;DTXSID50452318;AKOS030254864;MS-24577;PD193031;alpha -D-Mannopyranosylphenyl isothiocyanate;HY-132996;CS-0311655;4-Isothiocyanatophenyl-alpha-D-mannopyranoside;E75367;W-204140

Chemical Property of 4-Isothiocyanatophenyl alpha-D-mannopyranoside

Chemical Property:

• Melting Point: 180-181掳C
• Refractive Index: 1.659
• Boiling Point: 577.5±50.0 °C(Predicted)
• PKA: 12.73±0.70(Predicted)
• PSA: 143.83000
• Density: 1.56±0.1 g/cm3(Predicted)
• LogP: -0.40040
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated, Sonicated
• XLogP3: 1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 313.06200837
• Heavy Atom Count: 21
• Complexity: 383

Purity/Quality:

98%, ^*data from raw suppliers

4-Isothiocyanatophenyl α-D-Mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1N=C=S)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1N=C=S)O[C@@H]2[C@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: 4-Isothiocyanatophenyl α-D-Mannopyranoside is used as a novel mannose-based antigen delivery system that utilizes a polyamidoamine (PAMAM) dendrimer.

Technology Process of 4-Isothiocyanatophenyl alpha-D-mannopyranoside

There total 5 articles about 4-Isothiocyanatophenyl alpha-D-mannopyranoside 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:

4-nitrophenyl-α-D-mannopyranoside (10357-27-4) → [p-isothiocyanato]-phenyl α-D-mannopyranoside (96345-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: red. agent

2: H₂O

With red. agent; In water;

DOI:10.1016/S0040-4039(97)00760-0

Reference yield:

thiophosgene (463-71-8) + p-aminophenyl-α-D-mannopyranoside (34213-86-0) → [p-isothiocyanato]-phenyl α-D-mannopyranoside (96345-79-8)

Guidance literature:

In water; Yield given;

DOI:10.1016/S0040-4039(97)00760-0

Reference yield:

(4-isothiocyanato-phenyl)-(tetra-O-acetyl-ξ-D-glucopyranoside) (121814-40-2) → (4-isothiocyanato-phenyl)-ξ-D-glucopyranoside (20581-41-3,20581-45-7,20721-62-4,96345-79-8,146194-63-0)

Guidance literature:

With methanol; ammonia;

upstream raw materials:

(4-isothiocyanato-phenyl)-(tetra-O-acetyl-ξ-D-glucopyranoside)

4-hydroxyphenyl isothiocyanate

4-amino-phenol

thiophosgene

Downstream raw materials:

bis-{N-[20-p-(α-D-mannopyranosyloxy)phenylthioureidohexaethyleneglycolyl]-1H-[1,2,3]-triazole-4-yl-methyl}-11,11′-disulphanediyl diundecanoic acid diamide

N-{20-[p-(α-D-mannopyranosyloxy)-phenylthioureidohexaethyleneglycolyl]-1H-[1,2,3]-triazole-4-yl-methyl}-11-thioacetyl-undecanoic acid amide

Refernces