3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate
• CAS No.: 389119-61-3
• Molecular Formula: C₃₁H₃₂Cl₃NO₇
• Molecular Weight: 636.957
• Mol file: 389119-61-3.mol

Synonyms:3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

Chemical Property of 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

There total 9 articles about 3-O-acetyl-2,4,6-tri-O-benzyl-β-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: 75.0%

trichloroacetonitrile (545-06-2) + Acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-4-yl ester (127875-29-0) → 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate (389119-61-3)

Guidance literature:

With sodium hydride; In dichloromethane; at 22 ℃; for 1h;

DOI:10.1016/S0008-6215(01)00222-1

Reference yield:

allyl 4,6-O-benzylidene-β-D-galactopyranoside (71925-95-6) → 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate (389119-61-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 81 percent / Bu₃SnO; tetrabutylammonium iodide / Heating

2.1: 59 percent / 80 percent aq AcOH / 0.83 h / 86 °C

3.1: NaH (in oil) / 24 °C

4.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1 h / 24 °C

5.1: 1.04 g / Py

6.1: RhCl(PPh₃)3 / ethanol; toluene; H₂O / 20 h / Heating

6.2: 81 percent / 2N HCl / 1 h / Heating

7.1: 75 percent / 60 percent NaH / CH₂Cl₂ / 1 h / 22 °C

With pyridine; RhCl(PPh₃)3; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In ethanol; dichloromethane; water; toluene;

DOI:10.1016/S0008-6215(01)00222-1

Reference yield:

allyl β-D-galactopyranoside (2595-07-5,821794-45-0) → 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate (389119-61-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 70 percent / 0.5 h / 22 °C

2.1: 81 percent / Bu₃SnO; tetrabutylammonium iodide / Heating

3.1: 59 percent / 80 percent aq AcOH / 0.83 h / 86 °C

4.1: NaH (in oil) / 24 °C

5.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1 h / 24 °C

6.1: 1.04 g / Py

7.1: RhCl(PPh₃)3 / ethanol; toluene; H₂O / 20 h / Heating

7.2: 81 percent / 2N HCl / 1 h / Heating

8.1: 75 percent / 60 percent NaH / CH₂Cl₂ / 1 h / 22 °C

With pyridine; RhCl(PPh₃)3; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In ethanol; dichloromethane; water; toluene;

DOI:10.1016/S0008-6215(01)00222-1

upstream raw materials:

trichloroacetonitrile

Acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-4-yl ester

allyl 4,6-O-benzylidene-β-D-galactopyranoside

allyl β-D-galactopyranoside

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

2-propenyl 2,4-O-benzyl-3-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside