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

Base Information

• Chemical Name: 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((3aS,4S,5aR,8R,9aR,9bS)-2-oxo-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 115533-53-4
• Molecular Formula: C₄₄H₄₃NO₁₂S
• Molecular Weight: 809.891
• Mol file: 115533-53-4.mol

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

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

There total 27 articles about 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((3aS,4S,5aR,8R,9aR,9bS)-2-oxo-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-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) → ethyl O-(4,6-O-benzylidene-2,3-O-carbonyl-β-D-mannopyranosyl)-(1->4)-3,6-dibenzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-53-4)

Guidance literature:

Multi-step reaction with 8 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

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

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

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → ethyl O-(4,6-O-benzylidene-2,3-O-carbonyl-β-D-mannopyranosyl)-(1->4)-3,6-dibenzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-53-4)

Guidance literature:

Multi-step reaction with 8 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

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

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) → ethyl O-(4,6-O-benzylidene-2,3-O-carbonyl-β-D-mannopyranosyl)-(1->4)-3,6-dibenzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-53-4)

Guidance literature:

Multi-step reaction with 9 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

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

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

upstream raw materials:

C₅₁H₄₉F₃N₂O₁₄S₂

benzaldehyde dimethyl acetal

1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose

2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-α-D-glucopyranosyl bromide

Downstream raw materials:

C₇₇H₇₀N₂O₁₉

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

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

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