tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside
CAS No.:525593-50-4
Molecular Formula:C₂₆H₃₉N₃O₈Si
Molecular Weight:549.696
Hs Code.:

Synonyms:tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

There total 8 articles about tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-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: 96.0%

: 40608-06-8
levulinic anhydride

: 444118-29-0
6-O-acetyl-2-azido-3-O-benzyl-4-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside

: 525593-50-4
tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1002/chem.200390009

Reference yield:

: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 525593-50-4
tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 29.8 g / imidazole / CH₂Cl₂ / 2 h

2: NaOMe; MeOH / 0.25 h

3: 29.0 g / p-TsOH*H₂O / acetonitrile / 20 °C

4: 95 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 8 h

5: 92 percent / aq. TFA / CH₂Cl₂ / 8.5 h / 20 °C

6: 96 percent / 2,4,6-collidine / -40 °C

7: 96 percent / DMAP / CH₂Cl₂ / 5 h / 20 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; 4 A molecular sieve; sodium methylate; toluene-4-sulfonic acid; trifluoroacetic acid; silver(l) oxide; In dichloromethane; acetonitrile;
DOI:10.1002/chem.200390009

Reference yield:

: 99049-67-9
tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

: 525593-50-4
tert-butyldimethylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 29.0 g / p-TsOH*H₂O / acetonitrile / 20 °C

2: 95 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 8 h

3: 92 percent / aq. TFA / CH₂Cl₂ / 8.5 h / 20 °C

4: 96 percent / 2,4,6-collidine / -40 °C

5: 96 percent / DMAP / CH₂Cl₂ / 5 h / 20 °C

With 2,4,6-trimethyl-pyridine; dmap; 4 A molecular sieve; toluene-4-sulfonic acid; trifluoroacetic acid; silver(l) oxide; In dichloromethane; acetonitrile;
DOI:10.1002/chem.200390009