(6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one

Base Information

• Chemical Name: (6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one
• CAS No.: 174504-18-8
• Molecular Formula: C₂₉H₂₉NO₄
• Molecular Weight: 455.554

Synonyms:(6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one

Chemical Property of (6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one

Chemical Property:

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Technology Process of (6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one

There total 6 articles about (6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one 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: 70.0%

(E)-3-((2R,3R,4S,5R)-1-Allyl-3,4,5-tris-benzyloxy-6-oxo-piperidin-2-yl)-acrylic acid methyl ester (174504-17-7) → (6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one (174504-18-8)

Guidance literature:

ruthenium carbene complex (5percent w/w); In toluene; at 110 ℃; for 48h;

DOI:10.1016/0040-4039(95)02237-6

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (77174-08-4) → (6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one (174504-18-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / KOH (50percent) / tetrabutylammonium iodide / H₂O; CH₂Cl₂

2: FeCl₃

3: NH₃ / methanol

4: Dess Martin periodane

5: 85 percent

6: 70 percent / ruthenium carbene complex (5percent w/w) / toluene / 48 h / 110 °C

With potassium hydroxide; ammonia; iron(III) chloride; Dess-Martin periodane; ruthenium carbene complex (5percent w/w); tetra-(n-butyl)ammonium iodide; In methanol; dichloromethane; water; toluene;

DOI:10.1016/0040-4039(95)02237-6

Reference yield:

(3R,4S,5R,6R)-1-Allyl-3,4,5-tris-benzyloxy-6-hydroxymethyl-piperidin-2-one (174504-15-5) → (6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one (174504-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Dess Martin periodane

2: 85 percent

3: 70 percent / ruthenium carbene complex (5percent w/w) / toluene / 48 h / 110 °C

With Dess-Martin periodane; ruthenium carbene complex (5percent w/w); In toluene;

DOI:10.1016/0040-4039(95)02237-6

upstream raw materials:

(E)-3-((2R,3R,4S,5R)-1-Allyl-3,4,5-tris-benzyloxy-6-oxo-piperidin-2-yl)-acrylic acid methyl ester

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one

(3R,4S,5R,6R)-1-Allyl-3,4,5-tris-benzyloxy-6-hydroxymethyl-piperidin-2-one

(2S,3R,4S,5R)-1-Allyl-3,4,5-tris-benzyloxy-6-oxo-piperidine-2-carbaldehyde

Downstream raw materials:

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine

(1S,6R,7S,8R,8aR)-1-hydroxy-6,7,8-tris(benzyloxy)indolizidin-5-one

(3aR,3bS,4R,5S,6R,8aS)-4,5,6-Tris-benzyloxy-2,2-dioxo-hexahydro-1,3-dioxa-2λ⁶-thia-7a-aza-cyclopenta[a]inden-7-one

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