O^α-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester

Base Information

• Chemical Name: O^α-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester
• CAS No.: 252044-69-2
• Molecular Formula: C₄₀H₃₂O₉
• Molecular Weight: 656.689

Synonyms:O^α-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester

Chemical Property of O^α-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester

Chemical Property:

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Technology Process of O^α-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester

There total 7 articles about O^α-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester 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: 90.0%

L-mandeloyl-L-mandelic acid methyl ester (252044-67-0) + Oα-(9-fluorenylmethyloxycarbonyl)-L-mandelic acid (252044-61-4) → Oα-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester (252044-69-2)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jo981580+

Reference yield:

(S)-Mandelic acid (17199-29-0) → Oα-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester (252044-69-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / p-TsOH / CHCl₃ / 4 - 20 °C

2: 93 percent / diisopropylcarbodiimide; 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 20 °C

3: 91 percent / p-TsOH / methanol / 1.5 h

4: 90 percent / diisopropylcarbodiimide; 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 20 °C

With dmap; toluene-4-sulfonic acid; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; chloroform; 1: Etherification / 2: Esterification / 3: THP deprotection / 4: Esterification;

DOI:10.1021/jo981580+

Reference yield:

(S)-Methyl mandelate (21210-43-5) → Oα-(9-fluorenylmethyloxycarbonyl)-L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester (252044-69-2)

Guidance literature:

Multi-step reaction with 5 steps

1: p-TsOH

3: 93 percent / diisopropylcarbodiimide; 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 20 °C

4: 91 percent / p-TsOH / methanol / 1.5 h

5: 90 percent / diisopropylcarbodiimide; 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 20 °C

With dmap; toluene-4-sulfonic acid; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; 1: Etherification / 2: Hydrolysis / 3: Esterification / 4: THP deprotection / 5: Esterification;

DOI:10.1021/jo981580+

upstream raw materials:

L-mandeloyl-L-mandelic acid methyl ester

O^α-(9-fluorenylmethyloxycarbonyl)-L-mandelic acid

(S)-Phenyl-[(tetrahydro-pyran-2-yloxy)]-acetic acid methyl ester

(S)-Mandelic acid

Downstream raw materials:

L-mandeloyl-D-mandeloyl-L-mandelic acid methyl ester

L-mandeloyl-L-mandeloyl-L-mandelic acid methyl ester

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