(3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one

Base Information

• Chemical Name: (3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one
• CAS No.: 436845-29-3
• Molecular Formula: C₂₃H₂₇NO₉S
• Molecular Weight: 493.535

Synonyms:(3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one

Chemical Property of (3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one

There total 3 articles about (3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-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: 67.0%

norborn-2-ene (498-66-8) + carbon monoxide (201230-82-2) + (2E)-4,5,6-tri-O-acetyl-1,2,3-trideoxy-1-(N-propargyl-tosylamino)-D-erythro-hex-2-enose (436845-26-0) → Acetic acid (E)-(S)-1-((R)-1,2-diacetoxy-ethyl)-4-[((3aS,4S,7R,7aS)-1-oxo-3a,4,5,6,7,7a-hexahydro-1H-4,7-methano-inden-2-ylmethyl)-(toluene-4-sulfonyl)-amino]-but-2-enyl ester + (3aS,4R)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one + (3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one (436845-29-3)

Guidance literature:

carbon monoxide; (2E)-4,5,6-tri-O-acetyl-1,2,3-trideoxy-1-(N-propargyl-tosylamino)-D-erythro-hex-2-enose; With dicobalt octacarbonyl; In dichloromethane; at 20 ℃; for 0.75h;

norborn-2-ene; In dichloromethane; at 20 ℃;

With N-methyl-2-indolinone; In dichloromethane; at 0 - 20 ℃;

DOI:10.1080/07328300600732733

Reference yield:

carbon monoxide (201230-82-2) + (2E)-4,5,6-tri-O-acetyl-1,2,3-trideoxy-1-(N-propargyl-tosylamino)-D-erythro-hex-2-enose (436845-26-0) → (3aS,4R)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one + (3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one (436845-29-3)

Guidance literature:

carbon monoxide; (2E)-4,5,6-tri-O-acetyl-1,2,3-trideoxy-1-(N-propargyl-tosylamino)-D-erythro-hex-2-enose; dicobalt octacarbonyl; In dichloromethane; for 0.75h;

With N-methyl-2-indolinone; In dichloromethane; at 0 - 20 ℃; for 1h; Further stages.;

DOI:10.1021/jo011129+

Reference yield:

carbon monoxide (201230-82-2) + (2E)-4,5,6-tri-O-acetyl-1,2,3-trideoxy-1-(N-propargyl-tosylamino)-D-erythro-hex-2-enose (436845-26-0) → (3aR,4E,2'S)-4-(2',3'-diacetoxypropylidene)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one + (3aS,4E,2'S)-4-(2',3'-diacetoxypropylidene)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one + (3aS,4R)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one + (3aR,4S)-4-(tri-O-acetyl-D-erythro-triol-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one (436845-29-3)

Guidance literature:

carbon monoxide; (2E)-4,5,6-tri-O-acetyl-1,2,3-trideoxy-1-(N-propargyl-tosylamino)-D-erythro-hex-2-enose; dicobalt octacarbonyl; In dichloromethane; for 0.75h;

With N-methyl-2-indolinone; In dichloromethane; at 0 - 20 ℃; for 6h;

DOI:10.1021/jo011129+

upstream raw materials:

carbon monoxide

(2E)-4,5,6-tri-O-acetyl-1,2,3-trideoxy-1-(N-propargyl-tosylamino)-D-erythro-hex-2-enose

norborn-2-ene

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