Benzoic acid (2R,3S,4S,6S)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,6S)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester
• CAS No.: 65011-79-2
• Molecular Formula: C₂₉H₄₂O₇
• Molecular Weight: 502.648
• Mol file: 65011-79-2.mol

Synonyms:

Chemical Property of Benzoic acid (2R,3S,4S,6S)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4S,6S)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

There total 18 articles about Benzoic acid (2R,3S,4S,6S)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-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: 40.0%

Benzoic acid (2R,3S,4S,6S)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-((E)-3-oxo-oct-1-enyl)-tetrahydro-pyran-4-yl ester (65011-78-1) → Benzoic acid (2R,3S,4S,6S)-2-((E)-(R)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester (65027-24-9) + Benzoic acid (2R,3S,4S,6S)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester (65011-79-2)

Guidance literature:

With zinc borohydride; In 1,2-dimethoxyethane; diethyl ether; for 3h; Ambient temperature;

DOI:10.1139/v81-126

Reference yield:

methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-erythro-hexopyranosid-4-ulose (65011-68-9) → Benzoic acid (2R,3S,4S,6S)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester (65011-79-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 48.6 percent / potassium tert-butoxide / toluene / 8 h / Ambient temperature

2: 92 percent / H₂ / 20percent palladium hydroxide on charcoal / methanol; ethyl acetate / 24 h

3: 85 percent / potassium carbonate / methanol / 60 h

4: DIBAH / toluene / 0.5 h / -78 °C

5: 1.) lithium bis(trimethylsilyl)amide / 1.) HMPT, 20 min, room temperature; 2.) CH₂Cl₂/methanol/ether

6: 89 percent / pyridine / Ambient temperature

7: 89.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

8: 91 percent / chromium trioxide-pyridine, / CH₂Cl₂ / 30 h

9: 79 percent / diethyl ether / 3 h / Ambient temperature

10: 40 percent / zinc borohydride / 1,2-dimethoxy-ethane; diethyl ether / 3 h / Ambient temperature

With pyridine; chromium trioxide pyridine; zinc borohydride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; lithium hexamethyldisilazane; palladium hydroxide - carbon; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1139/v81-126

Reference yield:

methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribo-hexopyranoside (65011-67-8) → Benzoic acid (2R,3S,4S,6S)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester (65011-79-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, pyridine, trifluoroacetic acid / dimethylsulfoxide

2: 48.6 percent / potassium tert-butoxide / toluene / 8 h / Ambient temperature

3: 92 percent / H₂ / 20percent palladium hydroxide on charcoal / methanol; ethyl acetate / 24 h

4: 85 percent / potassium carbonate / methanol / 60 h

5: DIBAH / toluene / 0.5 h / -78 °C

6: 1.) lithium bis(trimethylsilyl)amide / 1.) HMPT, 20 min, room temperature; 2.) CH₂Cl₂/methanol/ether

7: 89 percent / pyridine / Ambient temperature

8: 89.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

9: 91 percent / chromium trioxide-pyridine, / CH₂Cl₂ / 30 h

10: 79 percent / diethyl ether / 3 h / Ambient temperature

11: 40 percent / zinc borohydride / 1,2-dimethoxy-ethane; diethyl ether / 3 h / Ambient temperature

With pyridine; chromium trioxide pyridine; zinc borohydride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium hexamethyldisilazane; palladium hydroxide - carbon; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1139/v81-126

upstream raw materials:

Benzoic acid (2R,3S,4S,6S)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-((E)-3-oxo-oct-1-enyl)-tetrahydro-pyran-4-yl ester

methyl 6-O-(tert-butyldiphenylsilyl)-4-C-(carboxymethyl)-2,4-dideoxy-α-D-ribo-hexopyranoside, γ-lactone

methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-erythro-hexopyranosid-4-ulose

methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-ribo-hexopyranoside