10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester

Base Information

• Chemical Name: 10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester
• CAS No.: 908835-50-7
• Molecular Formula: C₅₂H₇₁NO₈
• Molecular Weight: 838.138
• Mol file: 908835-50-7.mol

Synonyms:10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester

Chemical Property of 10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester

There total 7 articles about 10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl 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:

28-O-benzyl-3-O-[2-acetamido-2-deoxy-β-D-glucopyranosyl]oleanolic ester + benzaldehyde dimethyl acetal (1125-88-8) → 10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester (908835-50-7)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/j.bmcl.2006.05.086

Reference yield:

Oleanolic acid (508-02-1) → 10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester (908835-50-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / aq. K₂CO₃ / tetrahydrofuran / 20 °C

2: 96 percent / TMSOTf / CH₂Cl₂ / 0 - 20 °C

3: H₂NCH₂CH₂NH₂ / butan-1-ol / 90 °C

4: pyridine / 20 °C

5: NaOMe / CH₂Cl₂; methanol / 20 °C

6: DL-camphorsulfonic acid / dimethylformamide / 70 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; potassium carbonate; ethylenediamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1016/j.bmcl.2006.05.086

Reference yield:

benzyl bromide (100-39-0) → 10-(7-acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester (908835-50-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / aq. K₂CO₃ / tetrahydrofuran / 20 °C

2: 96 percent / TMSOTf / CH₂Cl₂ / 0 - 20 °C

3: H₂NCH₂CH₂NH₂ / butan-1-ol / 90 °C

4: pyridine / 20 °C

5: NaOMe / CH₂Cl₂; methanol / 20 °C

6: DL-camphorsulfonic acid / dimethylformamide / 70 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; potassium carbonate; ethylenediamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1016/j.bmcl.2006.05.086

upstream raw materials:

benzaldehyde dimethyl acetal

28-O-benzyl-3-O-[2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl]oleanolic ester

28-O-benzyl 3-O-[3′,4′,6′-tri-O-acetyl-2′-deoxy-2′-phthalimido-β-D-glucopyranosyl] oleanolic ester

Oleanolic acid

Downstream raw materials:

C₈₆H₉₇NO₁₇