methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Base Information

• Chemical Name: methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate
• CAS No.: 616876-62-1
• Molecular Formula: C₄₄H₅₇N₃O₁₃Si
• Molecular Weight: 864.034
• Mol file: 616876-62-1.mol

Synonyms:methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Chemical Property of methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

There total 13 articles about methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate 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%

benzonitrile (100-47-0) + methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate (616876-61-0) → methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate (616876-62-1)

Guidance literature:

With triethylamine; In acetonitrile; at -40 ℃;

DOI:10.1002/ejoc.200300210

Reference yield:

benzyl bromide (100-39-0) → methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate (616876-62-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / NaH; TBAI / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -40 °C

3: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3 h

4: 85 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.33 h / -10 °C

5: 90 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 20 °C

6: 93 percent / pyridine / 72 h / 0 - 20 °C

7: 89 percent / EtSH; pTsOH / CH₂Cl₂ / 3 h

8: 91 percent / Et₃N / acetonitrile / -40 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.200300210

Reference yield:

2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (138889-14-2) → methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate (616876-62-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -40 °C

2: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3 h

3: 85 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.33 h / -10 °C

4: 90 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 20 °C

5: 93 percent / pyridine / 72 h / 0 - 20 °C

6: 89 percent / EtSH; pTsOH / CH₂Cl₂ / 3 h

7: 91 percent / Et₃N / acetonitrile / -40 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.200300210

upstream raw materials:

benzonitrile

methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

benzyl bromide

2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose