[3,4,5-triacetyloxy-6-(cyanomethylsulfanyl)oxan-2-yl]methyl Acetate

Base Information

• Chemical Name: [3,4,5-triacetyloxy-6-(cyanomethylsulfanyl)oxan-2-yl]methyl Acetate
• CAS No.: 61145-33-3
• Molecular Formula: C16H21NO9S
• Molecular Weight: 403.41
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID30392021
• Mol file: 61145-33-3.mol

Synonyms:[3,4,5-triacetyloxy-6-(cyanomethylsulfanyl)oxan-2-yl]methyl Acetate;[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(cyanomethylsulfanyl)oxan-2-yl]methyl acetate;Cyanomethyl-2,3,4,6-tetra-O-acetyl-a-D-thiomannopyranoside;61145-39-9;AC1MPLI3;Oprea1_562394;SCHEMBL14262064;DTXSID30392021;AKOS030242539;FT-0624138;[(2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl)thio]acetonitrile;Cyanomethyl 2,3,4,6-tetra-O-acetyl-1-thio- beta -D-galactopyranoside

Chemical Property of [3,4,5-triacetyloxy-6-(cyanomethylsulfanyl)oxan-2-yl]methyl Acetate

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 7.08E-10mmHg at 25°C
• Melting Point: 95-97 °C
• Refractive Index: 1.514
• Boiling Point: 493.4 °C at 760 mmHg
• Flash Point: 252.2 °C
• PSA: 163.52000
• Density: 1.33 g/cm³
• LogP: 0.32628
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Ether (Slightly), Ethyl Aceta
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 403.09370242
• Heavy Atom Count: 27
• Complexity: 629

Purity/Quality:

98%Min ^*data from raw suppliers

Cyanomethyl 2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)SCC#N)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: The nitrile of the cyanomethyl group can be converted to a methyl imidate group by treatment with sodium methoxide or HCl which can be used to attach the sugar to a protein The nitrile of the cyanomethyl group can be converted to a methyl imidate group by treatment with sodium methoxide or HCl which can be used to attach the sugar to a protein.

Technology Process of [3,4,5-triacetyloxy-6-(cyanomethylsulfanyl)oxan-2-yl]methyl Acetate

There total 6 articles about [3,4,5-triacetyloxy-6-(cyanomethylsulfanyl)oxan-2-yl]methyl Acetate 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: 91.0%

chloroacetonitrile (107-14-2) + 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide (40591-65-9,51224-13-6,51898-28-3,57030-42-9,106818-92-2) → cyanomethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (61145-33-3)

Guidance literature:

With sodium disulfite; potassium carbonate; In water; acetone;

DOI:10.1002/anie.200461832

Reference yield: 77.0%

2-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-thiouronium bromide + chloroacetonitrile (107-14-2) → cyanomethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (61145-33-3)

Guidance literature:

With potassium carbonate; sodium hydrogensulfite; In water; acetone; at 20 ℃; for 3h; Cooling with ice;

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → cyanomethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (61145-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / acetone / Heating

2: 91 percent / K₂CO₃; sodium metabisulfite / acetone; H₂O

With sodium disulfite; potassium carbonate; In water; acetone;

DOI:10.1002/anie.200461832

upstream raw materials:

chloroacetonitrile

2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

β-D-galactose peracetate

Downstream raw materials:

2-imino-2-methoxyethyl-1-thio-β-D-galactopyranoside

cyanomethyl 1-thio-β-D-galactopyranoside

Refernces

• 1、 Pearce, Oliver M. T.,Fisher, Kerry D.,Humphries, Julia,Seymour, Leonard W.,Smith, Alberto,Davis, Benjamin G.. "Glycoviruses: Chemical glycosylation retargets adenoviral gene transfer". . p. 1057 - 1061. Retrieved 2007/10/03.