(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde

Base Information

• Chemical Name: (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde
• CAS No.: 193271-77-1
• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.392

Synonyms:(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde

Chemical Property of (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde

There total 7 articles about (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde 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: 85.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside (193271-74-8) → (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene-2-carbaldehyde (193271-77-1)

Guidance literature:

With lithium perchlorate; In acetonitrile; for 18h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00225-5

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene-2-carbaldehyde (193271-77-1)

Guidance literature:

Multi-step reaction with 6 steps

1: CSA / CHCl₃ / Heating

2: NaH, N-tosylimidazole / dimethylformamide / 2.5 h / Ambient temperature

3: benzene / 20 h / Ambient temperature

4: DIPEA, LiClO₄, DMAP, TsCl / acetonitrile / 16 h / 0 - 20 °C

5: DIBAL-H / CH₂Cl₂ / 0.25 h / -98 °C

6: 85 percent / LiClO₄ / acetonitrile / 18.5 h / Ambient temperature

With dmap; camphor-10-sulfonic acid; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; N-tosylimidazole; In dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(97)10370-7

Reference yield:

methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (272113-74-3) → (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene-2-carbaldehyde (193271-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / CH₂Cl₂ / 0.25 h / -98 °C

2: 85 percent / LiClO₄ / acetonitrile / 18.5 h / Ambient temperature

With lithium perchlorate; diisobutylaluminium hydride; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(97)10370-7

upstream raw materials:

cyclopenta-1,3-diene

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside

benzaldehyde dimethyl acetal

methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Downstream raw materials:

C₂₀H₂₂O₆

(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carboxylic acid methyl ester

(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-2-(1-oxopropyl)-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene

(1S,2S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-2-iodomethyl-4-methoxy-8-methyl-7-oxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester

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