5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine

Base Information

• Chemical Name: 5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine
• CAS No.: 1277100-47-6
• Molecular Formula: C₄₂H₇₀N₄O₁₈S
• Molecular Weight: 951.1
• Mol file: 1277100-47-6.mol

Synonyms:

Chemical Property of 5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine

There total 2 articles about 5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine 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:

C40H68N4O18 (1000022-40-1) → 5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine (1277100-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere

2: N,N-dimethyl-formamide / 19 h / 70 °C / Inert atmosphere

With pyridine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201002065

Reference yield:

C47H74N4O20S + potassium thioacetate (10387-40-3) → 5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine (1277100-47-6)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 19h; Inert atmosphere;

DOI:10.1002/chem.201002065

Reference yield:

5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine (1277100-47-6) + trifluoroacetic acid (76-05-1) → 5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine

Guidance literature:

5-O-(2-(tioacetyl)ethyl)-4-O-{2',6'-dideoxy-3',4'-bis-O-(acetyl)-2',6'-bis(tert-butoxycarbonylamino)-α-D-glucopyranosyl}-6-O-(acetyl)-N,N'-bis(tert-butoxycarbonylamino)-2-deoxystreptamine; With sodium methylate; In methanol; at 20 ℃; for 1.5h; Inert atmosphere;

trifluoroacetic acid; With chlorotriisopropylsilane; ethane-1,2-dithiol; at 20 ℃; for 1h;

DOI:10.1002/chem.201002065

upstream raw materials:

C₄₀H₆₈N₄O₁₈

potassium thioacetate