methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Base Information

Chemical Name:methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate
CAS No.:496780-12-2
Molecular Formula:C₄₄H₅₇N₃O₁₂Si
Molecular Weight:848.035
Hs Code.:

methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Synonyms:methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

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Chemical Property of methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

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Technology Process of methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

There total 12 articles about methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate 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: 93.0%

: 108-24-7
acetic anhydride

: 382614-17-7
methyl [dimethylthexylsilyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

: 496780-12-2
methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Guidance literature:: With pyridine; for 48h;
DOI:10.1139/v02-023

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 496780-12-2
methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaOMe; 4-dimethylaminopyridine; TfN₃ / methanol / 50 h / 20 °C

1.2: 71 percent / pTsOH / dimethylformamide / 48 h / 40 °C

2.1: 70 percent / imidazole / CH₂Cl₂ / 2 h / -10 °C

3.1: 85 percent / NaH; TBAI / CH₂Cl₂ / 24 h / 20 °C

4.1: 100 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -40 °C

5.1: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3 h

6.1: 85 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.33 h / -10 °C

7.1: 90 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 20 °C

8.1: 93 percent / pyridine / 72 h / 0 - 20 °C

With 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; triflic azide; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; dichloromethane; water;
DOI:10.1002/ejoc.200300210

Reference yield:

: 138923-10-1
2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

: 496780-12-2
methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / NaH; TBAI / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -40 °C

3: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 3 h

4: 85 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.33 h / -10 °C

5: 90 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 20 °C

6: 93 percent / pyridine / 72 h / 0 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; water;
DOI:10.1002/ejoc.200300210