Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Base Information

• Chemical Name: Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester
• CAS No.: 855282-34-7
• Molecular Formula: C₃₅H₄₉NO₁₃
• Molecular Weight: 691.773
• Mol file: 855282-34-7.mol

Synonyms:Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Chemical Property of Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

There total 8 articles about Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-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: 48.0%

Acetic acid (S)-1-acetoxymethyl-2-((4aS,6R,8S,8aR)-4-amino-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethyl ester (855282-32-5) + (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid (175085-05-9) → Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (855282-34-7) + C(10)-epi-mycalamide

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ja050728l

Reference yield:

Acetic acid (4R,4aS,8S,8aR)-6-(2,3-dihydroxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl ester → Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (855282-34-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / DMAP / CH₂Cl₂

2: 26.8 mg / TMSN₃; TMSOTf / acetonitrile / 1 h / -78 - 0 °C

3: H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

4: 48 percent / DMAP; DCC / CH₂Cl₂ / 12 h / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/ja050728l

Reference yield:

Acetic acid 2-((4aS,8S,8aR)-4-acetoxy-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-1-acetoxymethyl-ethyl ester → Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (855282-34-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 26.8 mg / TMSN₃; TMSOTf / acetonitrile / 1 h / -78 - 0 °C

2: H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

3: 48 percent / DMAP; DCC / CH₂Cl₂ / 12 h / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/ja050728l

upstream raw materials:

Acetic acid (S)-1-acetoxymethyl-2-((4aS,6R,8S,8aR)-4-amino-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethyl ester

(S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid

(R)-1-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)ethane-1,2-diol

(R)-1-((2R,5R,6R)-2-Methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethanol

Downstream raw materials:

mycalamide A