tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate
• CAS No.: 955021-69-9
• Molecular Formula: C₃₅H₅₃N₅O₈S
• Molecular Weight: 703.901
• Mol file: 955021-69-9.mol

Synonyms:tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate

Chemical Property of tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate

There total 12 articles about tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate 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:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate (955021-69-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: sodium tetrahydroborate; ethanol / 20 °C

2.1: pyridine; phosphorus tribromide / diethyl ether / 3 h / 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice

3.2: 20 °C / Cooling with acetone-dry ice

4.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C

5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice

6.2: 16.17 h / -78 °C / Cooling with acetone-dry ice

7.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C

7.2: 0 °C

8.1: dichloromethane / 14 h / 20 °C

9.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C

10.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C

11.1: sodium hydride / dimethyl sulfoxide / 1 h / 20 °C

11.2: 1 h / 20 °C

12.1: acetonitrile / 0.33 h / 90 °C / Microwave

13.1: acetonitrile / 0.33 h / 90 °C / Microwave

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; lithium borohydride; n-butyllithium; ethanol; water; iodine; sulfur trioxide pyridine complex; phosphorus tribromide; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;

Reference yield:

tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-methoxy-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate + phenethylamine (64-04-0) → tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate (955021-69-9)

Guidance literature:

In acetonitrile; at 90 ℃; for 0.333333h; Microwave;

Reference yield:

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one (145589-03-3) → tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-(phenethylamino)-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate (955021-69-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice

1.2: 20 °C / Cooling with acetone-dry ice

2.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C

3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice

4.2: 16.17 h / -78 °C / Cooling with acetone-dry ice

5.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C

5.2: 0 °C

6.1: dichloromethane / 14 h / 20 °C

7.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C

8.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C

9.1: sodium hydride / dimethyl sulfoxide / 1 h / 20 °C

9.2: 1 h / 20 °C

10.1: acetonitrile / 0.33 h / 90 °C / Microwave

11.1: acetonitrile / 0.33 h / 90 °C / Microwave

With 1H-imidazole; hydrogenchloride; lithium borohydride; n-butyllithium; water; iodine; sulfur trioxide pyridine complex; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

phenethylamine

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

tert-butyl (1S,3S)-3-(3-(3-methoxypropoxy)-4-methoxybenzyl)-4-methyl-1-((R)-oxiran-2-yl)pentylcarbamate

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one