2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate
• CAS No.: 616861-65-5
• Molecular Formula: C₃₇H₃₆Cl₃NO₈
• Molecular Weight: 729.054
• Mol file: 616861-65-5.mol

Synonyms:

Chemical Property of 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

There total 7 articles about 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 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: 63.0%

trichloroacetonitrile (545-06-2) + 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-D-galactopyranose → 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate (616861-67-7) + 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (616861-65-5)

Guidance literature:

With potassium carbonate; In dichloromethane;

DOI:10.1016/S0008-6215(03)00195-2

Reference yield:

D-galactose pentaacetate (25878-60-8) → 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (616861-65-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: HBr / acetic acid; CH₂Cl₂ / 1.5 h / 20 °C

1.2: 86 percent / 2,6-lutidine; Bu₄NBr / nitromethane / 20 h / 40 °C

2.1: 81 percent / KOH / tetrahydrofuran / 3 h / Heating

3.1: 77 percent / TMSOTf / CH₂Cl₂ / 2 h / 0 °C

4.1: 98 percent / NaOMe / 20 - 50 °C

5.1: 0.386 g / 1,3-dicyclohexylcarbodiimide; DMAP / tetrahydrofuran / 16 h / Heating

6.1: 1,4-diazabicyclo[2.2.2]octane / Rh(PPh₃)Cl / ethanol; toluene; H₂O / 17 h / Heating

6.2: 0.339 g / HgCl₂; HgO / acetone; H₂O / 6 h / 20 °C

7.1: 19 percent / K₂CO₃ / CH₂Cl₂

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; sodium methylate; potassium carbonate; dicyclohexyl-carbodiimide; Rh(PPh₃)Cl; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; toluene;

DOI:10.1016/S0008-6215(03)00195-2

Reference yield:

allyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside (162466-65-1) → 2-O-p-methoxybenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (616861-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 0.386 g / 1,3-dicyclohexylcarbodiimide; DMAP / tetrahydrofuran / 16 h / Heating

2.1: 1,4-diazabicyclo[2.2.2]octane / Rh(PPh₃)Cl / ethanol; toluene; H₂O / 17 h / Heating

2.2: 0.339 g / HgCl₂; HgO / acetone; H₂O / 6 h / 20 °C

3.1: 19 percent / K₂CO₃ / CH₂Cl₂

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; potassium carbonate; dicyclohexyl-carbodiimide; Rh(PPh₃)Cl; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1016/S0008-6215(03)00195-2

upstream raw materials:

trichloroacetonitrile

D-galactose pentaacetate

allyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside

3,4,6-tri-O-acetyl-α-D-galactopyranose-1,2-O-diyl allyl orthoacetate