methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose

Base Information

• Chemical Name: methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose
• CAS No.: 132867-72-2
• Molecular Formula: C₂₇H₂₃FO₇
• Molecular Weight: 478.474

Synonyms:methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose

Chemical Property of methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose

Chemical Property:

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Technology Process of methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose

There total 3 articles about methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose 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%

1,2,3-tri-O-benzoyl-6-deoxy-α-L-galactopyranose (132867-76-6) → methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose (132867-72-2) + methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-4-fluoro-α-L-glucopyranose (132867-71-1)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(91)80150-L

Reference yield:

6-deoxy-L-galactose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) → methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose (132867-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / pyridine / 0.2 h / -40 °C

2: 15 percent / diethylaminosulfur trifluoride (DAST) / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; diethylamino-sulfur trifluoride; In dichloromethane;

DOI:10.1016/0008-6215(91)80150-L

Reference yield:

benzoyl chloride (98-88-4) → methyl 1,2,3-tri-O-benzoyl-4,6-dideoxy-5(R)-fluoro-β-D-threo-hexopyranose (132867-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / pyridine / 0.2 h / -40 °C

2: 15 percent / diethylaminosulfur trifluoride (DAST) / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; diethylamino-sulfur trifluoride; In dichloromethane;

DOI:10.1016/0008-6215(91)80150-L

upstream raw materials:

1,2,3-tri-O-benzoyl-6-deoxy-α-L-galactopyranose

6-deoxy-L-galactose

benzoyl chloride

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