2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate

Base Information

Chemical Name:2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate
CAS No.:197243-30-4
Molecular Formula:C₃₂H₂₈Cl₃NO₁₀
Molecular Weight:692.934
Hs Code.:

Synonyms:2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate

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Chemical Property of 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate

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Technology Process of 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate

There total 7 articles about 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-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: 88.0%

: 545-06-2
trichloroacetonitrile

: 2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-D-galactopyranose

: 197243-30-4
2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1081/CAR-120026455

Reference yield:

: 143571-58-8
2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

: 197243-30-4
2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -50 °C

2: MeONa / 1 h / 20 °C

3: H₂; acetic acid / Pd/C / 6 h / 20 °C

4: 73 percent / pyridine / 12 h / 20 °C

5: 98 percent / CF₃CO₂H / CH₂Cl₂ / 1 h / 0 - 20 °C

6: 88 percent / DBU / CH₂Cl₂ / 3 h / 0 °C

With pyridine; oxalyl dichloride; hydrogen; sodium methylate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; 1: Swern oxidation / 2: Wittig-Horner carboxymethylenation;
DOI:10.1081/CAR-120026455

Reference yield:

: 197243-26-8
(2R,3S,5S,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-one

: 197243-30-4
2,4,6-tri-O-benzoyl-3-deoxy-3-C-[(methoxycarbonyl)methyl]-α-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: MeONa / 1 h / 20 °C

2: H₂; acetic acid / Pd/C / 6 h / 20 °C

3: 73 percent / pyridine / 12 h / 20 °C

4: 98 percent / CF₃CO₂H / CH₂Cl₂ / 1 h / 0 - 20 °C

5: 88 percent / DBU / CH₂Cl₂ / 3 h / 0 °C

With pyridine; hydrogen; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; 1: Wittig-Horner carboxymethylenation;
DOI:10.1081/CAR-120026455