1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose

Base Information

• Chemical Name: 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose
• CAS No.: 140658-54-4
• Molecular Formula: C₃₈H₄₂O₇S
• Molecular Weight: 642.813

Synonyms:1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose

Chemical Property of 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose

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Technology Process of 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose

There total 2 articles about 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose 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: 40.0%

1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C--α-D-glucopyranose (140658-53-3) → 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose (140658-54-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 100 ℃; for 2.5h;

DOI:10.1021/jo00039a025

Reference yield:

2,3,4,6-Tetra-O-benzyl-1-C--α-D-glucopyranose (140658-49-7) → 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose (140658-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 39 percent / Et₃N, 4-(dimethylamino)pyridine / 18 h / 0 °C

2: 40 percent / Bu₃SnH, AIBN / toluene / 2.5 h / 100 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In toluene;

DOI:10.1021/jo00039a025

Reference yield: 31.0%

1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose (140658-54-4) → 3,4,5,7-Tetra-O-benzyl-2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptitol (95189-55-2) + 2-O-acetyl-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose (140658-55-5)

Guidance literature:

nickel; In 1,4-dioxane; at 80 ℃; for 1.5h;

DOI:10.1021/jo00039a025

upstream raw materials:

1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C--α-D-glucopyranose

2,3,4,6-Tetra-O-benzyl-1-C--α-D-glucopyranose

Downstream raw materials:

3,4,5,7-Tetra-O-benzyl-2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptitol

2-O-acetyl-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose

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