methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate

Base Information

• Chemical Name: methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate
• CAS No.: 119680-64-7
• Molecular Formula: C₁₈H₁₉NO₆S
• Molecular Weight: 377.418
• Mol file: 119680-64-7.mol

Synonyms:methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate

Chemical Property of methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate

There total 3 articles about methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate 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: 83.0%

methyl (1S,2R,4S,6R)-9-acetyl-2-hydroxy-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate (109586-31-4) + phenylcarbonochloridothioate (1005-56-7) → methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate (119680-64-7)

Guidance literature:

With dmap; In dichloromethane; for 26h; Ambient temperature;

DOI:10.1021/jo00392a046

Reference yield:

(1S,3R,7S,8R)-6-acetyl-4,9-dioxa-5-azatricyclo<6.2.1.03,7>undec-5-en-10-one (109586-30-3) → methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate (119680-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / K₂CO₃ / 0.5 h / Ambient temperature

2: 83 percent / DMAP / CH₂Cl₂ / 26 h / Ambient temperature

With dmap; potassium carbonate; In dichloromethane;

DOI:10.1021/jo00392a046

Reference yield:

N-(4-chloro-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl)acetamide (109667-78-9) → methyl (1S,2R,4S,6R)-9-acetyl-2-<(phenoxythionocarbonyl)oxy>-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate (119680-64-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / toluene / 18 h / Heating

2: 85 percent / K₂CO₃ / 0.5 h / Ambient temperature

3: 83 percent / DMAP / CH₂Cl₂ / 26 h / Ambient temperature

With dmap; potassium carbonate; In dichloromethane; toluene;

DOI:10.1021/jo00392a046

upstream raw materials:

methyl (1S,2R,4S,6R)-9-acetyl-2-hydroxy-7-oxa-8-azabicyclo<4.3.0>non-8-ene-4-carboxylate

phenylcarbonochloridothioate

N-(4-chloro-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl)acetamide

(1S,3R,7S,8R)-6-acetyl-4,9-dioxa-5-azatricyclo<6.2.1.0^3,7>undec-5-en-10-one

Downstream raw materials:

(+)-Phyllanthocin

(3aR,6S,7aR)-3-((3R,4R)-5-Benzyloxymethoxy-3-hydroxy-4-methyl-pentanoyl)-3a,4,5,6,7,7a-hexahydro-benzo[d]isoxazole-6-carboxylic acid methyl ester

(3aR,6S,7aR)-3-((3S,4R)-5-Benzyloxymethoxy-3-hydroxy-4-methyl-pentanoyl)-3a,4,5,6,7,7a-hexahydro-benzo[d]isoxazole-6-carboxylic acid methyl ester

(3aR,6S,7aR)-3-((3R,4R)-5-Benzyloxy-3-hydroxy-4-methyl-pentanoyl)-3a,4,5,6,7,7a-hexahydro-benzo[d]isoxazole-6-carboxylic acid methyl ester