(2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: (2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside
• CAS No.: 1456773-41-3
• Molecular Formula: C₃₅H₅₂O₆SSi
• Molecular Weight: 628.946
• Mol file: 1456773-41-3.mol

Synonyms:(2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Chemical Property of (2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

There total 6 articles about (2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-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: 79.0%

S-(2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tertbutyldimethylsilyl-1-thio-?-D-glucopyranoside (1334540-38-3) + pivaloyl chloride (3282-30-2) → (2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside (1456773-41-3)

Guidance literature:

With pyridine; dmap; at 0 - 80 ℃; Inert atmosphere;

DOI:10.1002/chem.201204518

Reference yield:

β-D-glucose pentaacetate (604-69-3) → (2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside (1456773-41-3)

Guidance literature:

Multi-step reaction with 5 steps

1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere

2: sodium methylate / methanol / Inert atmosphere

3: 10-camphorsulfonic acid / acetonitrile / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

5: pyridine; dmap / 0 - 80 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; boron trifluoride diethyl etherate; sodium methylate; 10-camphorsulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.201204518

Reference yield:

2-methyl-5-tert-butylthiophenol (7340-90-1) → (2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside (1456773-41-3)

Guidance literature:

Multi-step reaction with 5 steps

1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere

2: sodium methylate / methanol / Inert atmosphere

3: 10-camphorsulfonic acid / acetonitrile / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

5: pyridine; dmap / 0 - 80 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; boron trifluoride diethyl etherate; sodium methylate; 10-camphorsulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.201204518

upstream raw materials:

2-methyl-5-tert-butylthiophenol

β-D-glucose pentaacetate

S-(2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tertbutyldimethylsilyl-1-thio-?-D-glucopyranoside

pivaloyl chloride

Downstream raw materials:

(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

(2-methyl-5-tert-butylphenyl)-4,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

dibutyl 4,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-2-O-pivaloyl-β-D-glucopyranosidephosphate