1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose

Base Information

• Chemical Name: 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose
• CAS No.: 214001-50-0
• Molecular Formula: C₃₂H₃₄O₆S
• Molecular Weight: 546.684

Synonyms:1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose

Chemical Property of 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose

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Technology Process of 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose

There total 2 articles about 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose 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: 42.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + 3-thiophthalimide-2,4-pentanedione (107552-89-6) → 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose (152420-91-2) + 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose (214001-50-0)

Guidance literature:

With 2,6-dimethylpyridine; 3 Angstroem MS; In dimethyl sulfoxide; for 168h; Product distribution; Ambient temperature; other solvents;

DOI:10.1021/jo981047u

Reference yield: 29.0%

methanol (67-56-1) + 3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + 3-thiophthalimide-2,4-pentanedione (107552-89-6) → 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose (152420-91-2) + 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose (214001-50-0) + 3-((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ylsulfanyl)-pentane-2,4-dione + 3-((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ylsulfanyl)-pentane-2,4-dione

Guidance literature:

With 2,6-dimethylpyridine; for 72h; Ambient temperature;

DOI:10.1021/jo981047u

Reference yield: 73.0%

1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-β-D-mannopyranose (214001-50-0) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → (E)-3-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-3-ylsulfanyl]-4-hydroxy-pent-3-en-2-one

Guidance literature:

With benzenesulfonic acid; In dichloromethane; for 0.833333h;

DOI:10.1002/(SICI)1099-0690(199908)1999:8<1869::AID-EJOC1869<3.0.CO;2-A

upstream raw materials:

methanol

3,4,6-tri-O-benzyl-D-glucal

3-thiophthalimide-2,4-pentanedione

Downstream raw materials:

3,4,6-tri-O-benzyl-1-O,2-S-[2-(1S-hydroxyethyl)-1-methyl-1,2-ethenediyl]-2-thio-β-D-mannopyranose

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