(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

Base Information

• Chemical Name: (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
• CAS No.: 148017-71-4
• Molecular Formula: C₂₆H₃₃N₃O₈S₂
• Molecular Weight: 579.695

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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) → (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 (148017-71-4)

Guidance literature:

Multi-step reaction with 7 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

7: 1) AgNO₃, pyridine, 2) H₂S / 1) MeOH, CH₂Cl₂, H₂O, room temperature, 10 min

With pyridine; lithium borohydride; hydrogen sulfide; sodium hydride; silver nitrate; 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) → (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 (148017-71-4)

Guidance literature:

Multi-step reaction with 6 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

6: 1) AgNO₃, pyridine, 2) H₂S / 1) MeOH, CH₂Cl₂, H₂O, room temperature, 10 min

With pyridine; lithium borohydride; hydrogen sulfide; sodium hydride; silver nitrate; 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) → (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 (148017-71-4)

Guidance literature:

Multi-step reaction with 5 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

5: 1) AgNO₃, pyridine, 2) H₂S / 1) MeOH, CH₂Cl₂, H₂O, room temperature, 10 min

With pyridine; lithium borohydride; hydrogen sulfide; sodium hydride; silver nitrate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.7164/antibiotics.49.199

upstream raw materials:

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

(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

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