(3aS,4S,5aR,8R,9aR,9bS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-2-one

Base Information

Chemical Name:(3aS,4S,5aR,8R,9aR,9bS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-2-one
CAS No.:115533-51-2
Molecular Formula:C₄₂H₄₄O₁₂
Molecular Weight:740.804
Hs Code.:

(3aS,4S,5aR,8R,9aR,9bS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-2-one

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Chemical Property of (3aS,4S,5aR,8R,9aR,9bS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-2-one

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Technology Process of (3aS,4S,5aR,8R,9aR,9bS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-2-one

There total 21 articles about (3aS,4S,5aR,8R,9aR,9bS)-4-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-2-one 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:

: 115533-46-5
Trifluoro-methanesulfonic acid (4aR,6R,7R,8S,8aR)-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-phenylcarbamoyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

: 115533-51-2
methyl O-(4,6-O-benzylidene-2,3-O-carbonyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranose

Guidance literature:: With pyridine; In dichloromethane; at 70 ℃; Yield given;
DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

: 34368-66-6
1,2-O-isopropylidene-3-O-phenylcarbamoyl-α-D-glucofuranose

: 115533-51-2
methyl O-(4,6-O-benzylidene-2,3-O-carbonyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranose

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: 1.) silver triflate, molecular sieves 4 Angstroem / 1.) dichloromethane, r.t., 30 min, then to -40 deg C, 2.) dichloromethane, -10 deg C, 45 min

5: K₂CO₃ / methanol / 7 h / Ambient temperature

6: 54 percent HBF₄ / dimethylformamide; diethyl ether / 24 h / Ambient temperature

7: pyridine / CH₂Cl₂ / -15 °C

8: pyridine / CH₂Cl₂ / 70 °C

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

Reference yield:

: 115533-28-3
3-O-(N-phenylcarbamoyl)-D-glucopyranose

: 115533-51-2
methyl O-(4,6-O-benzylidene-2,3-O-carbonyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

2: 82 percent / 33 percent HBr-AcOH / CHCl₃ / 5.5 h / Ambient temperature

3: 1.) silver triflate, molecular sieves 4 Angstroem / 1.) dichloromethane, r.t., 30 min, then to -40 deg C, 2.) dichloromethane, -10 deg C, 45 min

4: K₂CO₃ / methanol / 7 h / Ambient temperature

5: 54 percent HBF₄ / dimethylformamide; diethyl ether / 24 h / Ambient temperature

6: pyridine / CH₂Cl₂ / -15 °C

7: pyridine / CH₂Cl₂ / 70 °C

With pyridine; dmap; tetrafluoroboric acid; 4 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; potassium carbonate; acetic acid; In methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90561-5