6-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ⁶-[1,2,6]thiadiazinane-2-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: 6-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ⁶-[1,2,6]thiadiazinane-2-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 175846-24-9
• Molecular Formula: C₄₅H₄₇N₃O₈S₂
• Molecular Weight: 822.015

Synonyms:

Chemical Property of 6-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ⁶-[1,2,6]thiadiazinane-2-carboxylic acid 4-methoxy-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 6-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ⁶-[1,2,6]thiadiazinane-2-carboxylic acid 4-methoxy-benzyl ester

There total 7 articles about 6-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ⁶-[1,2,6]thiadiazinane-2-carboxylic acid 4-methoxy-benzyl ester 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:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → 6-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ6-[1,2,6]thiadiazinane-2-carboxylic acid 4-methoxy-benzyl ester (175846-24-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 32.48 g / triethylamine / methanol / 0.33 h

2: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -30 °C

3: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min

4: 68 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 60 °C

5: 87.4 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

6: 1) NaH / 1) DMF, room temperature, 10 min, 2) 80 deg C, 3 h

With lithium borohydride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.7164/antibiotics.49.199

Reference yield:

(2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (104773-44-6) → 6-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ6-[1,2,6]thiadiazinane-2-carboxylic acid 4-methoxy-benzyl ester (175846-24-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -30 °C

2: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min

3: 68 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 60 °C

4: 87.4 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

5: 1) NaH / 1) DMF, room temperature, 10 min, 2) 80 deg C, 3 h

With lithium borohydride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.7164/antibiotics.49.199

Reference yield:

(2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylic acid methyl ester (148016-87-9) → 6-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ6-[1,2,6]thiadiazinane-2-carboxylic acid 4-methoxy-benzyl ester (175846-24-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min

2: 68 percent / LiBH₄ / tetrahydrofuran / 0.5 h / 60 °C

3: 87.4 percent / triethylamine / CH₂Cl₂ / 0.33 h / -30 °C

4: 1) NaH / 1) DMF, room temperature, 10 min, 2) 80 deg C, 3 h

With lithium borohydride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.7164/antibiotics.49.199

upstream raw materials:

(2S,4S)-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol methanesulfonate

(R)-4-hydroxy-L-proline ethyl ester

(2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

(2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

(1R,5S,6S)-2-[(3S,5S)-5-(1,1-dioxo-2-p-methoxybenzyloxycarbonyl-3,4,5,6-tetrahydro-1,2,6-thiadiazin-6-yl)methyl-1-p-methoxybenzyloxycarbonylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid p-methoxybenzyl ester

(2S,4S)-2-(1,1-dioxo-2-p-methoxybenzyloxycarbonyl-3,4,5,6-tetrahydro-1,2,6-thiadiazin-6-yl)methyl-4-mercapto-1-p-methoxybenzyloxycarbonylpyrrolidine

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