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

Base Information

Chemical Name:2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate
CAS No.:616861-68-8
Molecular Formula:C₃₆H₃₃Cl₃N₂O₉
Molecular Weight:744.025
Hs Code.:

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

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

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

There total 7 articles about 2-O-p-nitrobenzoyl-3,4,6-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: 39.0%

: 545-06-2
trichloroacetonitrile

: 2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-D-galactopyranose

: 616861-68-8
2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

: 616861-66-6
2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

Guidance literature:: With potassium carbonate; In dichloromethane;
DOI:10.1016/S0008-6215(03)00195-2

Reference yield:

: 25878-60-8
D-galactose pentaacetate

: 616861-68-8
2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

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: 0.587 g / 1,3-dicyclohexylcarbodiimide; DMAP / tetrahydrofuran / 0.5 h / 20 °C

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

6.2: 0.356 g / HgCl₂; HgO / acetone; H₂O / 6 h / 20 °C

7.1: 26 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:

: 162466-65-1
allyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside

: 616861-68-8
2-O-p-nitrobenzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 0.587 g / 1,3-dicyclohexylcarbodiimide; DMAP / tetrahydrofuran / 0.5 h / 20 °C

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

2.2: 0.356 g / HgCl₂; HgO / acetone; H₂O / 6 h / 20 °C

3.1: 26 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