(5-Acetamido-3,4-diacetyloxy-6-chlorooxan-2-yl)methyl acetate

Base Information

• Chemical Name: (5-Acetamido-3,4-diacetyloxy-6-chlorooxan-2-yl)methyl acetate
• CAS No.: 3068-34-6
• Molecular Formula: C14H20ClNO8
• Molecular Weight: 365.768
• Hs Code.: 2932990090
• NSC Number: 401827
• DSSTox Substance ID: DTXSID90952923
• Mol file: 3068-34-6.mol

Synonyms:(5-acetamido-3,4-diacetyloxy-6-chlorooxan-2-yl)methyl acetate;2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride;N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE;MFCD00069776;51236-40-9;NSC401827;2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-?-D-glucopyranosyl chloride;Chloro 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-alpha-D-glucopyranose;SCHEMBL10036889;SCHEMBL23479752;SCHEMBL24406814;DTXSID90952923;EINECS 221-325-6;2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-|A-D-glucopyranosyl chloride;AKOS024351483;NSC-401827;SB48294;SY052452;FT-0634637;B2705-106035;2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl chloride;3,4,6-Tri-O-acetyl-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranosyl chloride

Chemical Property of (5-Acetamido-3,4-diacetyloxy-6-chlorooxan-2-yl)methyl acetate

Chemical Property:

• Vapor Pressure: 9E-11mmHg at 25°C
• Melting Point: >214 °C (dec.)(lit.)
• Refractive Index: 117.5 ° (C=1, CHCl3)
• Boiling Point: 516.4 °C at 760 mmHg
• PKA: 13.22±0.70(Predicted)
• Flash Point: 266.1 °C
• PSA: 117.23000
• Density: 1.32 g/cm³
• LogP: 0.27220
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 365.0877443
• Heavy Atom Count: 24
• Complexity: 511

Purity/Quality:

98% ^*data from raw suppliers

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1Cl)COC(=O)C)OC(=O)C)OC(=O)C
• Uses: Chloro 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose (cas# 3068-34-6) is a useful reactant in the total synthesis of glycosylated human interferon-γ.

Technology Process of (5-Acetamido-3,4-diacetyloxy-6-chlorooxan-2-yl)methyl acetate

There total 32 articles about (5-Acetamido-3,4-diacetyloxy-6-chlorooxan-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: 90.0%

N-acetyl-D-glucosamine (14131-68-1) + acetyl chloride (75-36-5) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6)

Guidance literature:

at 4 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0029-1218818

Reference yield: 89.0%

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6)

Guidance literature:

With hydrogenchloride; acetic anhydride; In diethyl ether; at 3 ℃; for 72h;

DOI:10.1071/CH04176

Reference yield: 88.0%

Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6)

Guidance literature:

With hydrogenchloride; acetic anhydride; for 138h; Ambient temperature;

DOI:10.1016/0008-6215(95)00302-9

upstream raw materials:

2-acetamido-2-deoxy-D-glucose

acetyl chloride

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester

Downstream raw materials:

methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

N-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside

ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Refernces

SYNTHESIS OF A GLYCOTRIPEPTIDE AND A GLYCOSOMATOSTATIN CONTAINING THE 3-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-L-SERINE RESIDUE

10.1016/S0008-6215(00)85248-9

A study detailing the synthesis of a glycotripeptide and a glycosomatostatin, both containing the 3-O-(2-acetamido-2-deoxy-D-glucopyranosyl)-L-serine residue. The research was conducted by a team from the Salk Institute for Biological Studies and the University of California, San Diego. The process involved solid-phase synthesis to create the sequences Gly-[P-D-GlcpNAc-(1→3)-Ser]-Ala-OH and /I-D-GlcpNAc-(1→3)-Ser-13-somatostatin. The synthesized glycopeptides were found to be homogeneous upon examination through thin-layer chromatography (t.l.c.) and liquid chromatography (l.c.), and they exhibited the correct amino acid composition and 2-amino-2-deoxy-D-glucose content. The structure of one of the glycopeptides was confirmed by mass spectrometry and nuclear magnetic resonance (n.m.r.) spectroscopy. The study was supported by grants from the National Institute of Arthritis, Metabolism, and Digestive Diseases, the National Heart Institute, and the William Randolph Hearst Foundation, among others.