2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate

Base Information

Chemical Name:2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate
CAS No.:202647-51-6
Molecular Formula:C₄₄H₅₂Cl₃NO₁₄
Molecular Weight:925.254
Hs Code.:

Synonyms:2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate

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Chemical Property of 2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate

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Technology Process of 2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate

There total 15 articles about 2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose 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:

: 545-06-2
trichloroacetonitrile

: 2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-D-glucopyranose

: 2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-β-D-glucopyranose trichloroacetimidate

: 202647-51-6
2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate

Guidance literature:: With potassium carbonate; In dichloromethane; for 16h; Title compound not separated from byproducts.;
DOI:10.1002/1521-3765(20010216)7:4<858::AID-CHEM858>3.0.CO;2-N

Reference yield:

: 3370-81-8
3-O-methyl-D-glucopyranose

: 202647-51-6
2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / pyridine / 16 h

2: 59 percent / BF₃*Et₂O / toluene / 1.5 h

3: MeONa / methanol; CH₂Cl₂ / 0.5 h

4: CSA / acetonitrile / 1.5 h

5: 97 percent / NaH / dimethylformamide / 2 h

6: 60 percent / Et₃SiH, TFAA, TFA / 1,2-dichloro-ethane / 2 h

7: 93 percent / EDCI, DMAP / 3.5 h

8: 52 percent / NIS, trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 0.08 h / -25 °C

9: 76 percent / H₂, (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate / tetrahydrofuran / 0.17 h

10: 90 percent / HgCl₂, HgO / acetone; H₂O / 1 h

11: K₂CO₃ / CH₂Cl₂ / 16 h

With pyridine; triethylsilane; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; sodium methylate; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; trifluoroacetic anhydride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0960-894X(99)00155-9

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 202647-51-6
2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate

Guidance literature:: Multi-step reaction with 8 steps

1: CSA / acetonitrile / 1.5 h

2: 97 percent / NaH / dimethylformamide / 2 h

3: 60 percent / Et₃SiH, TFAA, TFA / 1,2-dichloro-ethane / 2 h

4: 93 percent / EDCI, DMAP / 3.5 h

5: 52 percent / NIS, trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 0.08 h / -25 °C

6: 76 percent / H₂, (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate / tetrahydrofuran / 0.17 h

7: 90 percent / HgCl₂, HgO / acetone; H₂O / 1 h

8: K₂CO₃ / CH₂Cl₂ / 16 h

With triethylsilane; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; trifluoroacetic anhydride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1016/S0960-894X(99)00155-9