tunicamycin III

Base Information

• Chemical Name: tunicamycin III
• CAS No.: 76544-45-1
• Molecular Formula: C₃₇H₆₀N₄O₁₆
• Molecular Weight: 816.901
• European Community (EC) Number: 636-028-0
• DSSTox Substance ID: DTXSID70746741
• Mol file: 76544-45-1.mol

Synonyms:tunicamycin III;Tunicamycin A2 homolog, ~90% (HPLC);DTXSID70746741;76544-45-1

Chemical Property of tunicamycin III

Chemical Property:

• PSA: 319.06000
• LogP: -0.63140
• Storage Temp.: ?20°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 20
• Exact Mass: 816.40043184
• Heavy Atom Count: 57
• Complexity: 1390

Purity/Quality:

97% ^*data from raw suppliers

TUNICAMYCIN A2 HOMOLOG 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC=CC(=O)NC1C(C(C(OC1OC2C(C(C(C(O2)CO)O)O)NC(=O)C)CC(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)O)O)O
• Isomeric SMILES: CCCCCCCCCCC/C=C/C(=O)NC1C(C(C(OC1OC2C(C(C(C(O2)CO)O)O)NC(=O)C)CC(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)O)O)O

Technology Process of tunicamycin III

There total 9 articles about tunicamycin III 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:

allyl 2-acetamido-2-deoxy-α-D-glucopyranoside (54400-75-8) → tunicamycin III (76544-45-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / p-toluenesulfonic acid

2: 93 percent / pyridine

3: 72 percent / SeO₂ / acetic acid

4: 19 percent / silver carbonate, silver oxide, silver perchlorate / CH₂Cl₂ / in dark

5: methanolic sodium methoxide

With pyridine; selenium(IV) oxide; sodium methylate; silver perchlorate; toluene-4-sulfonic acid; silver carbonate; silver(l) oxide; In dichloromethane; acetic acid;

DOI:10.1016/S0040-4039(01)81486-6

Reference yield:

allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside (95069-09-3) → tunicamycin III (76544-45-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / pyridine

2: 72 percent / SeO₂ / acetic acid

3: 19 percent / silver carbonate, silver oxide, silver perchlorate / CH₂Cl₂ / in dark

4: methanolic sodium methoxide

With pyridine; selenium(IV) oxide; sodium methylate; silver perchlorate; silver carbonate; silver(l) oxide; In dichloromethane; acetic acid;

DOI:10.1016/S0040-4039(01)81486-6

Reference yield:

2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propionyl-α-D-glucopyranose (95069-11-7) → tunicamycin III (76544-45-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 19 percent / silver carbonate, silver oxide, silver perchlorate / CH₂Cl₂ / in dark

2: methanolic sodium methoxide

With sodium methylate; silver perchlorate; silver carbonate; silver(l) oxide; In dichloromethane;

DOI:10.1016/S0040-4039(01)81486-6

upstream raw materials:

trans-tetradec-2-enoic acid

allyl 2-acetamido-2-deoxy-α-D-glucopyranoside

allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propionyl-α-D-glucopyranose

Refernces