tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate
• CAS No.: 953820-35-4
• Molecular Formula: C₂₉H₅₀N₂O₅
• Molecular Weight: 506.726
• Mol file: 953820-35-4.mol

Synonyms:tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate

Chemical Property of tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-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-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate

There total 13 articles about tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-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: 46.0%

tert-butyl (2S,3S,5S)-1-amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptan-3-ylcarbamate (953820-34-3) + 2,2-dimethylhexanoic acid (813-72-9) → tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate (953820-35-4)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 5h;

Reference yield:

tert-butyl (3(S)-benzyloxymethyl-1(S)-hydroxymethyl-4-methyl-pentyl)carbamate (861451-15-2) → tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate (953820-35-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.75 h / -60 - -50 °C

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

2.2: 1 h / 20 °C

3.1: methanol; ammonia; water / 18 h / 20 °C

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 0 - 20 °C

With methanol; oxalyl dichloride; ammonia; water; sodium hydride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; 1.1: Swern Oxidation;

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate (953820-35-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C

1.2: 21.5 h / 0 °C

2.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

3.2: 0 °C

4.1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 18 h / 0 - 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexanes / 1.25 h / -78 °C

5.2: 20.5 h / -78 - -20 °C

6.1: hydrogenchloride; water / acetonitrile / 1.5 h / 20 °C

6.2: 0 °C

7.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C

8.1: sodium tetrahydroborate / ethanol / 16 h / 20 °C

9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.75 h / -60 - -50 °C

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

10.2: 1 h / 20 °C

11.1: methanol; ammonia; water / 18 h / 20 °C

12.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 0 - 20 °C

With hydrogenchloride; methanol; lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; ammonia; water; dihydrogen peroxide; titanium tetrachloride; sodium hydride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexanes; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 9.1: Swern Oxidation;

upstream raw materials:

tert-butyl (2S,3S,5S)-1-amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptan-3-ylcarbamate

2,2-dimethylhexanoic acid

Benzyloxymethyl chloride

(2S,4S)-2-(tert-butoxycarbonyl)amino-4-(benzyloxymethyl)-5-methyl-hexanal