O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

Base Information

Chemical Name:O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose
CAS No.:104139-78-8
Molecular Formula:C₄₀H₄₂ClN₃O₁₅
Molecular Weight:840.238
Hs Code.:

O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

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Chemical Property of O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

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Technology Process of O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

There total 17 articles about O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose 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: 94.0%

: 104139-77-7
O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: 104139-78-8
O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

Guidance literature:: by acetolysis;
DOI:10.1016/S0040-4039(00)84054-X

Reference yield:

: 100-39-0
benzyl bromide

: 104139-78-8
O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

Guidance literature:: Multi-step reaction with 16 steps

1: 1) Bu₂SnO, 2) Bu₄NI / 1) toluene, 2) 100 deg C

3: F^(1-) / in aqueous media

4: by tosylation

5: NaH

6: N₃^(1-)

7: by benzylation

9: by tosylation

10: NaI

11: DBU

12: 2) H₂O₂, aq. NaHCO₃ / 1) hydroboration, CH₂Cl₂

14: CrO₃-3.5 M H₂SO₄ / acetone

16: 94 percent / by acetolysis

With chromium(VI) oxide; sulfuric acid; fluoride; dihydrogen peroxide; azide^(1-); tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In acetone;
DOI:10.1016/S0040-4039(00)84054-X

Reference yield:

: 97390-18-6
1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

: 104139-78-8
O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

Guidance literature:: Multi-step reaction with 16 steps

1: 1) Bu₂SnO, 2) Bu₄NI / 1) toluene, 2) 100 deg C

3: F^(1-) / in aqueous media

4: by tosylation

5: NaH

6: N₃^(1-)

7: by benzylation

9: by tosylation

10: NaI

11: DBU

12: 2) H₂O₂, aq. NaHCO₃ / 1) hydroboration, CH₂Cl₂

14: CrO₃-3.5 M H₂SO₄ / acetone

16: 94 percent / by acetolysis

With chromium(VI) oxide; sulfuric acid; fluoride; dihydrogen peroxide; azide^(1-); tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In acetone;
DOI:10.1016/S0040-4039(00)84054-X