ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 142072-53-5
• Molecular Formula: C₆₆H₇₉NO₃₀S
• Molecular Weight: 1398.41
• Mol file: 142072-53-5.mol

Synonyms:ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 22 articles about ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-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: 74.0%

ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (142072-52-4) + acetobromomannose (13242-53-0) → ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (142072-53-5)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; toluene; at -20 ℃; for 0.333333h;

DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

1,2-O-isopropylidene-3-O-phenylcarbamoyl-α-D-glucofuranose (34368-66-6) → ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (142072-53-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 87 percent / 0.05 M H₂SO₄ / dioxane / 5 h / 100 °C

2: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

3: 82 percent / 33 percent HBr-AcOH / CHCl₃ / 5.5 h / Ambient temperature

4: 94 percent / molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂; toluene / 45 h / -45 °C

5: K₂CO₃ / methanol / 4 h / Ambient temperature

6: 54 percent HBF₄ / dimethylformamide; diethyl ether

7: pyridine / CH₂Cl₂ / 2.5 h

8: 2.) 40 percent acetic acid / 1.) DMF, toluene, 2.) 1,4-dioxane, r.t., 4-5 h

9: 1.94 g / 0.1 percent sodium methoxide, methanol / CH₂Cl₂ / 0.17 h / Ambient temperature

10: 4-toluenesulfonic acid / benzene / 1 h / Ambient temperature

11: 80 percent acetic acid / 0.08 h / Ambient temperature

12: 1.) silver triflate, molecular sieves 4 Angstroem / 1.) dichloromethane, -50 deg C, 15 min, 2.) dichloromethane

13: 87 percent / 65 percent acetic acid / dioxane / 24 h / 75 °C

14: 74 percent / molecular sieves 4 Angstroem, silver triflate, N,N,N',N'-tetramethylurea / CH₂Cl₂; toluene / 0.33 h / -20 °C

With pyridine; methanol; dmap; tetrafluoroboric acid; 4 A molecular sieve; sulfuric acid; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; tetramethylurea; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)>-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (142072-53-5)

Guidance literature:

Multi-step reaction with 14 steps

1: HBF₄ / dimethylformamide; diethyl ether / 4 h / Ambient temperature

2: 1.) sodium hydride / 1.) N,N-dimethylformamide, r.t., 45 min, 2.) 50 deg C, 4 h

3: 86 percent / NaBH₃CN, molecular sieves 3 Angstroem, HCl / tetrahydrofuran; diethyl ether / 0 °C

4: 94 percent / molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂; toluene / 45 h / -45 °C

5: K₂CO₃ / methanol / 4 h / Ambient temperature

6: 54 percent HBF₄ / dimethylformamide; diethyl ether

7: pyridine / CH₂Cl₂ / 2.5 h

8: 2.) 40 percent acetic acid / 1.) DMF, toluene, 2.) 1,4-dioxane, r.t., 4-5 h

9: 1.94 g / 0.1 percent sodium methoxide, methanol / CH₂Cl₂ / 0.17 h / Ambient temperature

10: 4-toluenesulfonic acid / benzene / 1 h / Ambient temperature

11: 80 percent acetic acid / 0.08 h / Ambient temperature

12: 1.) silver triflate, molecular sieves 4 Angstroem / 1.) dichloromethane, -50 deg C, 15 min, 2.) dichloromethane

13: 87 percent / 65 percent acetic acid / dioxane / 24 h / 75 °C

14: 74 percent / molecular sieves 4 Angstroem, silver triflate, N,N,N',N'-tetramethylurea / CH₂Cl₂; toluene / 0.33 h / -20 °C

With pyridine; hydrogenchloride; methanol; tetrafluoroboric acid; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; tetramethylurea; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0008-6215(00)90561-5

upstream raw materials:

ethyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(2-O-acetyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

acetobromomannose

1,2-O-isopropylidene-3-O-phenylcarbamoyl-α-D-glucofuranose

benzaldehyde dimethyl acetal