3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
• CAS No.: 383905-66-6
• Molecular Formula: C₄₈H₅₂Cl₃NO₁₄
• Molecular Weight: 973.298

Synonyms:3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate

Chemical Property of 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate

Chemical Property:

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Technology Process of 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate

There total 9 articles about 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-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: 81.0%

trichloroacetonitrile (545-06-2) + 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-galactopyranose → 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate (383905-66-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1016/S0008-6215(01)00194-X

Reference yield:

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate (383905-66-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaOCH₃ / methanol / 2 h

2.1: dibutyltin oxide / toluene / 17 h / Heating

2.2: 87 percent / tetrabutylammonium iodide / toluene / 2 h / Heating

3.1: 69 percent / pyridine / 18 h / 20 °C

4.1: H₂ / Pd-C / methanol / 10 h / 20 °C

5.1: 69 percent / Me₃SiOTf; molecular sieves / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

6.1: 67 percent / ammonium cerium(IV) nitrate / acetone; H₂O / 5 h / 20 °C

7.1: 81 percent / DBU / CH₂Cl₂ / 4 h / 0 °C

With pyridine; molecular sieve; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water; acetone; toluene;

DOI:10.1016/S0008-6215(01)00194-X

Reference yield:

4-methoxyphenyl β-D-galactopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9) → 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate (383905-66-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dibutyltin oxide / toluene / 17 h / Heating

1.2: 87 percent / tetrabutylammonium iodide / toluene / 2 h / Heating

2.1: 69 percent / pyridine / 18 h / 20 °C

3.1: H₂ / Pd-C / methanol / 10 h / 20 °C

4.1: 69 percent / Me₃SiOTf; molecular sieves / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

5.1: 67 percent / ammonium cerium(IV) nitrate / acetone; H₂O / 5 h / 20 °C

6.1: 81 percent / DBU / CH₂Cl₂ / 4 h / 0 °C

With pyridine; molecular sieve; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water; acetone; toluene;

DOI:10.1016/S0008-6215(01)00194-X

upstream raw materials:

trichloroacetonitrile

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

2,3,4,6-tetra-O-benzyl-D-galactopyranose

4-methoxyphenyl β-D-galactopyranoside

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