methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-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-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate
CAS No.:616876-61-0
Molecular Formula:C₃₇H₅₃N₃O₁₂Si
Molecular Weight:759.926
Hs Code.:

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

There total 13 articles about methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-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: 89.0%

: 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

: 616876-61-0
methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Guidance literature:: With toluene-4-sulfonic acid; ethanethiol; In dichloromethane; for 3h;
DOI:10.1002/ejoc.200300210

Reference yield:

: 100-39-0
benzyl bromide

: 616876-61-0
methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Guidance literature:: Multi-step reaction with 7 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

7: 89 percent / EtSH; pTsOH / CH₂Cl₂ / 3 h

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; In tetrahydrofuran; pyridine; 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

: 616876-61-0
methyl [dimethylthexylsilyl 2-O-acetyl-4-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-L-idopyranoside]uronate

Guidance literature:: Multi-step reaction with 7 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

7: 89 percent / EtSH; pTsOH / CH₂Cl₂ / 3 h

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; In tetrahydrofuran; pyridine; dichloromethane; water;
DOI:10.1002/ejoc.200300210