methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

Base Information

Chemical Name:methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate
CAS No.:727991-21-1
Molecular Formula:C₄₅H₅₀Cl₆N₂O₁₅Si
Molecular Weight:1099.7
Hs Code.:

methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

Synonyms:methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

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Chemical Property of methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

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Technology Process of methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

There total 14 articles about methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside 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: 90.0%

: 545-06-2
trichloroacetonitrile

: methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α/β-D-galactopyranoside

: methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside trichloroacetimidate

: 727991-21-1
methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1021/ja0484045

Reference yield:

: 545-06-2
trichloroacetonitrile

: methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α/β-D-galactopyranoside

: 727991-21-1
methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.25h;

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 727991-21-1
methyl (2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside trichloroacetimidate

Guidance literature:: Multi-step reaction with 8 steps

1: 13 g / DL-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

2: 75 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 16 h

3: 79 percent / N-iodosuccinimide; triflic acid; 4A molecular sieves / CH₂Cl₂ / 0.17 h / 0 °C

4: 85 percent / Bu₄NF / tetrahydrofuran / 20 h / 20 °C

5: 74 percent / 4A molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -40 - -10 °C

6: 77 percent / RuCl₂(=CHPh)(PCy₃)(1,3-dimesityl-4,5-dihydroimidazolylidene) / CH₂Cl₂ / 2 h / 20 °C

7: 81 percent / pyridine; I₂; H₂O / tetrahydrofuran / 0.5 h / 20 °C

8: 90 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0484045