(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

Base Information

• Chemical Name: (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
• CAS No.: 201025-01-6
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 4 articles about (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 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: 76.0%

(1S,2R,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-2-(1-hydroxypropyl)-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene → (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-2-(1-oxopropyl)-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene (201025-01-6)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 0.25h;

DOI:10.1016/j.tet.2007.08.070

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-2-(1-oxopropyl)-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene (201025-01-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / LiClO₄ / acetonitrile / 18 h / 20 °C

2: Li / tetrahydrofuran

3: (COCl)2; DMSO; Et₃N

With oxalyl dichloride; lithium perchlorate; lithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; acetonitrile; 3: Swern oxidation;

DOI:10.1021/ol061390i

Reference yield:

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-2-(1-oxopropyl)-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene (201025-01-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / LiClO₄ / acetonitrile / 18 h / 20 °C

2: Li / tetrahydrofuran

3: (COCl)2; DMSO; Et₃N

With oxalyl dichloride; lithium perchlorate; lithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; acetonitrile; 3: Swern oxidation;

DOI:10.1021/ol061390i

upstream raw materials:

cyclopenta-1,3-diene

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

(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

Downstream raw materials:

(2R,4aR,6S,6aS,7S,9R,9aS,9bS)-6-Methoxy-2-phenyl-9a-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7,9-dicarbaldehyde

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