3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS No.: 401900-33-2
• Molecular Formula: C₅₉H₇₈O₂₇
• Molecular Weight: 1219.25

Synonyms:3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Chemical Property of 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Chemical Property:

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Technology Process of 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

There total 3 articles about 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 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: 60.0%

[(3aS,4R,6R,7R,7aS)-7-Benzyloxy-2,2-dimethyl-6-((3aR,5R,5aS,8aR,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-methanol + 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl trichloroacetimidate (401900-32-1) → 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (401900-33-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -45 ℃; for 2h;

DOI:10.1016/S0008-6215(01)00232-4

Reference yield:

Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2R,3S,4S,5R)-3,4,5-triacetoxy-6-hydroxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester → 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (401900-33-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / K₂CO₃ / CH₂Cl₂ / 24 h / Heating

2: 60 percent / trimethylsilyl trifluromethanesulfonate / CH₂Cl₂ / 2 h / -45 °C

With trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In dichloromethane;

DOI:10.1016/S0008-6215(01)00232-4

Reference yield:

3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-1,2,3,4-tetra-O-acetyl-α-D-galactopyranose → 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (401900-33-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / hydrazine acetate / dimethylformamide / 1.5 h

2: 70 percent / K₂CO₃ / CH₂Cl₂ / 24 h / Heating

3: 60 percent / trimethylsilyl trifluromethanesulfonate / CH₂Cl₂ / 2 h / -45 °C

With trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00232-4

upstream raw materials:

3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl trichloroacetimidate

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