4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: 4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside
• CAS No.: 1446762-11-3
• Molecular Formula: C₃₈H₄₆O₉SSi
• Molecular Weight: 706.929

Synonyms:4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside

Chemical Property of 4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside

There total 7 articles about 4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside 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:

p-tolyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-β-1-thio-D-galactopyranoside (1402044-32-9) + levulinic acid (123-76-2) → 4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside (1446762-11-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/asia.201201204

Reference yield:

4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (28244-94-2,28244-99-7,86782-41-4,131488-65-8) → 4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside (1446762-11-3)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium methylate / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere

3: camphor-10-sulfonic acid / acetonitrile / 0.5 h / 20 °C / Inert atmosphere

4: dmap; triethylamine / 0.5 h / Inert atmosphere

5: acetic acid / water / 0.5 h / Inert atmosphere

6: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; camphor-10-sulfonic acid; sodium methylate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/asia.201201204

Reference yield:

β-D-galactose peracetate (4163-60-4) → 4-methylphenyl 2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-1-thio-β-D-galactopyranoside (1446762-11-3)

Guidance literature:

Multi-step reaction with 7 steps

1: boron trifluoride diethyl etherate / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2: sodium methylate / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

3: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere

4: camphor-10-sulfonic acid / acetonitrile / 0.5 h / 20 °C / Inert atmosphere

5: dmap; triethylamine / 0.5 h / Inert atmosphere

6: acetic acid / water / 0.5 h / Inert atmosphere

7: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/asia.201201204

upstream raw materials:

4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

β-D-galactose peracetate

4-methylphenyl 6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

p-methylphenyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

(2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1→4)-2-trichloroacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl N-phenyltirfluoroacetimidate

(2,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1→4)-2-trichloroacetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl N-phenyltirfluoroacetimidate

C₄₅H₅₉NO₁₈Si

C₅₁H₆₁F₃N₂O₁₇Si

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