tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate

Base Information

• Chemical Name: tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate
• CAS No.: 1255212-85-1
• Molecular Formula: C₂₈H₅₂N₂O₅Si
• Molecular Weight: 524.817

Synonyms:tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate

Chemical Property of tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate

There total 7 articles about tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate 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: 92.0%

tert-butyl ((2R,3S)-2-((tert-butyldimethylsilyl)oxy)-4-(((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methyl-4-oxobutyl)(methyl)carbamate (1255212-77-1) → tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate (1255212-85-1)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 65 ℃; for 5h; Inert atmosphere;

DOI:10.1021/ja105119r

Reference yield:

(2S,3R)-4-((tert-butoxycarbonyl)(methyl)amino)-3-hydroxy-2-methylbutanoic acid (1255212-63-5) → tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate (1255212-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

2: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 65 °C / Inert atmosphere

With 2,6-dimethylpyridine; dimethylsulfide borane complex; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja105119r

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → tert-butyl((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)(methyl)carbamate (1255212-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

2: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 65 °C / Inert atmosphere

With 2,6-dimethylpyridine; dimethylsulfide borane complex; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja105119r

upstream raw materials:

(2S,3R)-4-((tert-butoxycarbonyl)(methyl)amino)-3-hydroxy-2-methylbutanoic acid

tert-butyl ((2R,3S)-2-((tert-butyldimethylsilyl)oxy)-4-(((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methyl-4-oxobutyl)(methyl)carbamate

t-butyldimethylsiyl triflate

p-methoxybenzyl chloride

Downstream raw materials:

tert-butyl ((((2R,3R)-5-(S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-3-methyl-10-nitro-6-oxo-3,4,5,6-tetrahydro-2H-benzo[b][1,5]oxazocin-2-yl)methyl)(methyl)carbamate

tert-butyl (((2R,3R)-10-amino-5-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-3-methyl-6-oxo-3,4,5,6-tetrahydro-2H-benzo[b][1,5]oxazocin-2-yl)methyl)(methyl)carbamate

tert-butyl(((2R,3R)-10-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-3-methyl-6-oxo-3,4,5,6-tetrahydro-2H-benzo[b][1,5]oxazocin-2-yl)methyl)(methyl)carbamate

tert-butyl-((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(2-fluoro-N-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-3-nitrobenzamido)-3-methylbutyl)(methyl)carbamate

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