Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 334934-34-8
• Molecular Formula: C₄₇H₅₁F₃N₂O₁₃
• Molecular Weight: 908.923

Synonyms:

Chemical Property of Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 8 articles about Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl 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:

benzaldehyde dimethyl acetal (1125-88-8) → Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (334934-34-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 561 mg / TsOH / dimethylformamide / 2 h / 50 °C

2: pyridine / 20 °C

With pyridine; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00002-7

Reference yield:

benzyl bromide (100-39-0) → Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (334934-34-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / NaH / dimethylformamide / 1.5 h / -20 - -15 °C

2: 87 percent / Me₃N*BH₃; AlCl₃; water / tetrahydrofuran / 6 h / 20 °C

3: 70 percent / AgOTf; Ms-4A / CH₂Cl₂ / 20 °C

4: MeONa / methanol / 20 °C

5: 561 mg / TsOH / dimethylformamide / 2 h / 50 °C

6: pyridine / 20 °C

With pyridine; aluminium trichloride; trimethylamine-borane; water; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00002-7

Reference yield:

N-[3-((2R,4aR,6R,7R,8R,8aS)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-propyl]-2,2,2-trifluoro-acetamide → Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (334934-34-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / NaH / dimethylformamide / 1.5 h / -20 - -15 °C

2: 87 percent / Me₃N*BH₃; AlCl₃; water / tetrahydrofuran / 6 h / 20 °C

3: 70 percent / AgOTf; Ms-4A / CH₂Cl₂ / 20 °C

4: MeONa / methanol / 20 °C

5: 561 mg / TsOH / dimethylformamide / 2 h / 50 °C

6: pyridine / 20 °C

With pyridine; aluminium trichloride; trimethylamine-borane; water; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00002-7

upstream raw materials:

benzonitrile

3-trifluoroacetamidopropyl (4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

benzaldehyde dimethyl acetal

benzyl bromide

Downstream raw materials:

Benzoic acid (2S,4aR,6S,7R,8S,8aS)-7-acetoxy-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

3-trifluoroacetamidopropyl (2-O-acetyl-3-O-benzoyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

3-trifluoroacetamidopropyl (3-O-benzoyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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