5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose

Base Information

• Chemical Name: 5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose
• CAS No.: 956317-00-3
• Molecular Formula: C₃₁H₃₂O₆
• Molecular Weight: 500.591

Synonyms:5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose

Chemical Property of 5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose

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Technology Process of 5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose

There total 3 articles about 5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose 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: 82.0%

3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-β-L-ido-pentofuranose (138847-59-3) + benzoic acid (65-85-0,8013-63-6) → 5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose (956317-00-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tet.2009.10.079

Reference yield:

3-O-benzyl-1,2-O-cyclohexylidene-α-D-xylo-pentodialdo-1,4-furanose (15354-75-3) → 5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose (956317-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / diethyl ether / 3.5 h / 0 °C

2: 79 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; 2: Mitsunobu reaction;

DOI:10.1021/ol701734s

Reference yield:

phenylmagnesium bromide → 5-O-benzoyl-3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-α-D-gluco-pentofuranose (956317-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / diethyl ether / 3.5 h / 0 °C

2: 79 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; 2: Mitsunobu reaction;

DOI:10.1021/ol701734s

upstream raw materials:

3-O-benzyl-1,2-O-cyclohexylidene-5-C-phenyl-β-L-ido-pentofuranose

benzoic acid

3-O-benzyl-1,2-O-cyclohexylidene-α-D-xylo-pentodialdo-1,4-furanose

Downstream raw materials:

3,6-anhydro-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone

(+)-goniofufurone

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