1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside

Base Information

• Chemical Name: 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside
• CAS No.: 158761-05-8
• Molecular Formula: C₂₇H₄₀N₄O₁₄S
• Molecular Weight: 676.699
• Mol file: 158761-05-8.mol

Synonyms:1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside

Chemical Property of 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside

There total 20 articles about 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside 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: 78.0%

monobromobimane (71418-44-5) + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4) → 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside (158761-05-8)

Guidance literature:

With sodium hydrogencarbonate; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/ol0362008

Reference yield: 75.0%

diethylphophoryl cyanide (418785-19-0) → 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside (158761-05-8)

Guidance literature:

With magnesium methanolate; In methanol; for 1h;

DOI:10.1021/ja017891a

Reference yield:

myo-inositol → 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside (158761-05-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 23 percent / p-toluenesulfonic acid / dimethylformamide; toluene / 24 h / Heating

2.1: bis(tributyltin)oxide / toluene / 3 h / Heating

2.2: 5.8 g / NaHCO₃ / toluene / 24 h

3.1: Ag₂O; 3 Angstroem molecular sieves / CH₂Cl₂ / 20 h / 20 °C

4.1: 93 percent / LAH / diethyl ether / 2 h / 20 °C

5.1: 44 percent / AgOTf; 2,6-diisopropyl-4-methyl-pyridine / CH₂Cl₂; diethyl ether

6.1: ethylene glycol; (+)-camphor sulfonic acid / acetonitrile / 6 h / 20 °C

7.1: 127.6 mg / pyridine / 16 h / 20 °C

8.1: 86 percent / H₂; HCl / Pd/C / ethyl acetate; H₂O / 5 h / 20 °C

9.1: 31 percent / diethylphophoryl cyanide; diisopropylethylamine / dimethylformamide / 13 h / 0 - 4 °C

10.1: 75 percent / Mg(OMe)2 / methanol / 1 h

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; diisopropyl-2,6-methyl-4-pyridine; diethyl cyanophosphonate; 3 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; ethylene glycol; magnesium methanolate; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; bis(tri-n-butyltin)oxide; silver(l) oxide; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja017891a

upstream raw materials:

diethylphophoryl cyanide

monobromobimane

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol

(R)-2-acetylamino-3-(acetylthio)propionic acid