2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 142072-49-9
• Molecular Formula: C₄₇H₅₁NO₁₂S
• Molecular Weight: 853.987

Synonyms:

Chemical Property of 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 18 articles about 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 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:

1,2-O-isopropylidene-3-O-phenylcarbamoyl-α-D-glucofuranose (34368-66-6) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (142072-49-9)

Guidance literature:

Multi-step reaction with 10 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

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; 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) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (142072-49-9)

Guidance literature:

Multi-step reaction with 10 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

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; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

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

Reference yield:

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((3aS,4S,5aR,9aR,9bS)-2-ethoxy-2-methyl-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (142072-49-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 0.3 M NaOMe / CH₂Cl₂; methanol / Ambient temperature

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

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

4: 86 percent / NaBH₃CN, molecular sieves 3 Angstroem, HCl / tetrahydrofuran; diethyl ether / 0 °C

5: 94 percent / molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂; toluene / 45 h / -45 °C

6: K₂CO₃ / methanol / 4 h / Ambient temperature

7: 54 percent HBF₄ / dimethylformamide; diethyl ether

8: pyridine / CH₂Cl₂ / 2.5 h

9: 2.) 40 percent acetic acid / 1.) DMF, toluene, 2.) 1,4-dioxane, r.t., 4-5 h

10: 1.94 g / 0.1 percent sodium methoxide, methanol / CH₂Cl₂ / 0.17 h / Ambient temperature

11: 4-toluenesulfonic acid / benzene / 1 h / Ambient temperature

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; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

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

upstream raw materials:

Triethyl orthoacetate

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

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

benzaldehyde dimethyl acetal

Downstream raw materials:

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

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

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

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

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