methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Base Information

Chemical Name:methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
CAS No.:496065-42-0
Molecular Formula:C₃₃H₃₉N₃O₉S
Molecular Weight:653.753
Hs Code.:

methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Synonyms:methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

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Chemical Property of methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

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Technology Process of methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

There total 7 articles about methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 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: 98.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 496065-40-8
methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 496065-42-0
methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Guidance literature:: In toluene; at 90 ℃; for 17h;
DOI:10.1139/v02-117

Reference yield:

: 96093-11-7
Methyl-2-azido-4,6-O-benzylidene-2-desoxy-β-D-galactopyranoside

: 496065-42-0
methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: N-iodosuccinimide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / -60 °C

1.2: 83 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / 3 h / -60 - -30 °C

2.1: 94 percent / sodium methoxide / methanol / 2 h

3.1: 82 percent / dimethyl sulfoxide; acetic anhydride / 20 °C

4.1: 92 percent / L-selectride / tetrahydrofuran / 1 h / 0 °C

5.1: 102 mg / tetrahydrofuran; H₂O / 0.5 h

6.1: 98 percent / toluene / 17 h / 90 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; acetic anhydride; L-Selectride; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 2.1: Zemplen transesterification;
DOI:10.1139/v02-117

Reference yield:

: phenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-1-thio-α,β-D-ribo-hexopyranoside

: 496065-42-0
methyl 2-acetamido-3-O-(4-O-benzyl-3,6-dideoxy-2-O-(imidazol-1-yl)thiocarbonyl-β-D-arabino-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: N-iodosuccinimide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / -60 °C

1.2: 83 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / 3 h / -60 - -30 °C

2.1: 94 percent / sodium methoxide / methanol / 2 h

3.1: 82 percent / dimethyl sulfoxide; acetic anhydride / 20 °C

4.1: 92 percent / L-selectride / tetrahydrofuran / 1 h / 0 °C

5.1: 102 mg / tetrahydrofuran; H₂O / 0.5 h

6.1: 98 percent / toluene / 17 h / 90 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; acetic anhydride; L-Selectride; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 2.1: Zemplen transesterification;
DOI:10.1139/v02-117