2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-α-D-galactopyranosyl chloride

Base Information

• Chemical Name: 2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-α-D-galactopyranosyl chloride
• CAS No.: 78878-51-0
• Molecular Formula: C₃₃H₄₁ClO₆Si
• Molecular Weight: 597.223
• Mol file: 78878-51-0.mol

Synonyms:

Chemical Property of 2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-α-D-galactopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-α-D-galactopyranosyl chloride

There total 13 articles about 2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-α-D-galactopyranosyl chloride 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:

allyl 6-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside (6207-47-2) → 2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-α-D-galactopyranosyl chloride (78878-51-0)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydride / benzene

2: hydrochloric acid (0.5M) / methanol

3: 1.) methanol, heating, 1 h; 2.) N,N-dimethylformamide, 100 deg C, 30 min

4: 81 percent / potassium tert-butoxide / dimethylformamide / 2 h / 85 °C

5: 84 percent / pyridine / 45 h / -35 - 20 °C

6: imidazole / dimethylformamide / 48 h / 70 °C

7: 70 percent / mercuric oxide, mercuric chloride / acetone; H₂O / 0.08 h / Ambient temperature

8: hexamethylphosphorous triamide, carbon tetrachloride / CH₂Cl₂ / 1.) -45 deg C, 1 h; 2.) room temperature

With 1H-imidazole; hydrogenchloride; tetrachloromethane; potassium tert-butylate; sodium hydride; mercury dichloride; mercury(II) oxide; Hexamethylphosphorous triamide; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0008-6215(00)80851-4

Reference yield:

benzoyl chloride (98-88-4) → 2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-α-D-galactopyranosyl chloride (78878-51-0)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 0.75 h / -35 - 20 °C

2: hydrochloric acid (0.5M) / methanol

3: 1.) methanol, heating, 1 h; 2.) N,N-dimethylformamide, 100 deg C, 30 min

4: 93 percent / diazabicyclo<2.2.2.>octane, tris(triphenylphosphine)rhodium(I) chloride / ethanol / 2 h / Heating

5: imidazole / dimethylformamide / 48 h / 70 °C

6: 70 percent / mercuric oxide, mercuric chloride / acetone; H₂O / 0.08 h / Ambient temperature

7: hexamethylphosphorous triamide, carbon tetrachloride / CH₂Cl₂ / 1.) -45 deg C, 1 h; 2.) room temperature

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; hydrogenchloride; tetrachloromethane; Wilkinson's catalyst; mercury dichloride; mercury(II) oxide; Hexamethylphosphorous triamide; In pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(00)80851-4

Reference yield:

2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-D-galactopyranose → 2-O-benzoyl-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-α-D-galactopyranosyl chloride (78878-51-0)

Guidance literature:

With tetrachloromethane; Hexamethylphosphorous triamide; In dichloromethane; 1.) -45 deg C, 1 h; 2.) room temperature;

DOI:10.1016/S0008-6215(00)80851-4

upstream raw materials:

allyl 6-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside

allyl 6-O-benzyl-2-O-(2-butenyl)-3,4-O-isopropylidene-α-D-galactopyranoside

allyl 6-O-benzyl-2-O-(2-butenyl)-α-D-galactopyranoside

benzyl bromide