tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
CAS No.:920958-33-4
Molecular Formula:C₄₉H₆₁N₃O₁₂Si
Molecular Weight:912.122
Hs Code.:

Synonyms:tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 6 articles about tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 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: 80.0%

: methyl 2-O-acetyl-3,4-di-O-benzyl-L-idopyranosiduronate trichloroacetimidate

: 120312-09-6
tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid

: 920958-33-4
tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 - -10 ℃; for 1.5h;
DOI:10.1002/chem.200601103

Reference yield:

: (2S,3S,4R,5R)-3,4-Bis-benzyloxy-5,6-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 920958-33-4
tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 203 mg / imidazole / CH₂Cl₂ / 40 h / -25 °C

2: 96 percent / DMAP / pyridine / 20 °C

3: 88 percent / HF*pyridine / tetrahydrofuran / 28 h / 20 °C

4: 98 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 20 °C

5: 80 percent / TMSOTf / CH₂Cl₂ / 1.5 h / -25 - -10 °C

With 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1002/chem.200601103

Reference yield:

: (3aR,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-carboxylic acid methyl ester

: 920958-33-4
tert-butyldimethylsilyl (methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: trifluoroacetic acid / CH₂Cl₂; H₂O / 4 h / 20 °C

2: 203 mg / imidazole / CH₂Cl₂ / 40 h / -25 °C

3: 96 percent / DMAP / pyridine / 20 °C

4: 88 percent / HF*pyridine / tetrahydrofuran / 28 h / 20 °C

5: 98 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 20 °C

6: 80 percent / TMSOTf / CH₂Cl₂ / 1.5 h / -25 - -10 °C

With 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; water;
DOI:10.1002/chem.200601103